I’ve put together one hundred tips for dating with your self-esteem in tow. My suggestions will help you to be mindful, date with your eyes and ears open, to come from a place of personal security, and to be aware of what to look for when considering progressing from dating into a fully-fledged relationship.


1. If you can’t date without losing the ability to love, trust, care for and respect yourself, don’t date or be in a relationship until you can. You will find that you have much better dating experiences when you like and love you.

2. No matter how much your body and your imagination screams yes, leave sex out of the first few dates, longer if possible. If you have sex before you get to know someone or as a means of getting to know someone, it will cloud your judgement and is likely to put you in The Justifying Zone, that special mental place that we go to when we sexually or emotionally invest too soon and look, or should I say, scratch around, for reasons to justify the initial investment because we don’t like to think that we’ve slept with someone who is not appropriate for us.

3. Dating is a discovery phase. It’s a getting to know you period where you can get a sense of how much you click as well as whether you have enough going on to forge a relationship. This period is for you to learn about the other party even if what you learn spells the end of your involvement.

4. Contrary to popular opinion, the key thing that you need to discover is whether you share common core values – this is what will take you from dating into a bona fide relationship. If you rely on sexual chemistry and common interests and forget to discover whether you share common values and the other landmarks of healthy and successful relationships, you will mistake personality for character, lust and attraction for the presence of shared core values, and will ultimately struggle to understand why you cannot move forward with somebody with whom you believe you have so much in common.

5. All that someone being very good at sex tells you is that they’re very good at sex and/or very practised at it. All that someone who you feel a physical/sexual attraction to when you know nothing about their character or suitability tells you is that you are horny based on their appearance and the illusion of what they might be. Be careful of thinking that because someone knows your body very well or how to make it ‘sing’ that they know you very well. If they don’t know you before they have sex with you, they still won’t know you after they have sex with you.

6. Don’t make dating into a vocation. Have fun! While I appreciate that you’ve got to get out there and meet people, it shouldn’t be done to the exclusion of having a life otherwise every date will carry more meaning and weight than is warranted. It will feel as if it’s a painful interview and it’ll become a numbers game.

7. Don’t date if you are not over your ex. It may feel like the best thing to do is jump back into the saddle after a break up but if you haven’t given yourself time to get over it, you are likely to end up sabotaging your dates. It is also likely that the emotions that are still attached to your ex will create drama in itself. Never date until you have reduced your baggage to hand luggage. Oh and of course it’s not fair on the people you’re dating!

8. Online dating is an option for meeting people but not your only option. Getting out there and meeting people like they used to do in ‘olden times’ (the time before t’internet), is still the most effective way. If you are going to date online, you need the hide of a rhino, good detective skills, and a willingness and ability not to let your imagination run wild.

9. No ex on the first date! In fact, you have no real reason to talk about your ex on the first few dates. The only reason is if there is something about your ex that is vitally important that they know. Example: They’re stalking you and anyone you date, you have a child together etc. You’re supposed to be getting to know each other and if you talk about your exes you may actually end up communicating that you’re still emotionally invested.

10. Don’t start acting like you’re in a relationship when you’re are just dating. Slow your roll! You’re going too fast! If you do this, you will expect as if you’re in a relationship when you don’t actually know each other enough to do this. You will make the other person nervy if you go into girlfriend/boyfriend mode when you’ve not established whether you’re in a relationship or in fact don’t even know them. Don’t assume the position!

11. Don’t make exceptions to your normal boundaries. It’s better to be yourself and know your limits. If you’re already making exceptions for someone you are dating, it is a sign of not so great things to come. As dating is a discovery phase where you should be aware of things that potentially signal a relationship not happening, turning a blind eye to what may be code amber and code red stuff is not in your interests.

12. Remember to act like you’re worthy and in the same league. Do not put people on a pedestal because the only place for them to look at you is from above, which means you are beneath them.This creates a dangerous, imbalanced relationship that is difficult to recover from. Be careful of getting dazzled by someone and in awe of them as it may make you blind to the reality plus it puts undue pressure on them creating expectations that they cannot live up to. They’re just not that special!

13. There are some people who won’t live up to the hype they created on the first few dates. Don’t spend from here to eternity trying to recreate that ‘persona’ that they exhibited as some people are very good at putting on a performance at the start but quickly fade into the ‘real’ them. If what you saw has disappeared that quickly, trust me when I say it wasn’t real. People unfold.

14. If someone is saying that they want to get to know you by getting your knickers down, they’re not trying to get to know you. They’re trying to charm and disarm you so that they can shag you.

15. Dating doesn’t require you to be blind, whether it’s to the reality of someone or to your own needs. For you to have a sense of who they are, the relationship or the possibility of one, and whether it feels good for you, you need to be capable of engaging with them with your eyes and ears open. The dating shouldn’t be one-sided and if your needs can’t be met while you run around meeting theirs, it is a sign of a dangerous, imbalanced relationship.

16. Just because someone is interested in you it doesn’t mean that you have to reciprocate. It is totally okay for you not to be interested and they are not entitled to reciprocation.

17. If you have a ‘type’ and so far it has failed to yield a successful, healthy, fulfilling relationship, it’s safe to say that you need to let go of whatever preconceived ideas that you hold about the type of person you are attracted to or who is ‘right’ for you.

18. Boundaries are vital in dating and act as your personal electric fence. It is important for you to know your limits and act in accordance, otherwise you will communicate to your dates that not only do you not respect yourself enough but that they are free to take advantage of you. Shady people will exploit your lack of boundaries and will quickly work out what they can get away with and act accordingly. If you want to be with somebody who treats and regards you with love, care, trust, and respect, make sure that you also do these for you.

19. Get rid of anyone who only communicates with you via text message. You’re not a booty call.

20. Never assume that because someone has shown interest, asked you out or is even dating you, that they are single or willing, able, and ready for a relationship. You’d be surprised how many people get asked out by attached people!

21. Somewhere between date one and three, you need to clarify that the person is single and that they are not married, with somebody, living with an ex, just separated, long-term separated etc. If you don’t know the answer to these questions, as in you have asked and clarified, or you are afraid to ask, do not pass GO. Basically do not go past date 3 without knowing this information. Ever. Certainly don’t sleep with them without knowing this vital information.

22. If you don’t want to spend a lot of time wrecking your head over whether they really like you, whether they’ll call or why they didn’t call, keep your knickers/pants on for the first few dates at least. Sex whilst it can be very enjoyable confuses the hell out of things. If you’re asking where you stand when you’ve already had sex, it’s already too late. You’re closing the door after the horse has bolted.

23. Don’t make assumptions about what type of person someone will be based on their job or how much money they make. You’re clouding your judgement by drawing misplaced conclusions about people. Examine your generalisations and preconceived ideas.

24. Get a life with some variety that opens you up to meeting new people and having new experiences. You are not going to meet someone doing the same hard and fast routine day in day out, week in, week out. Someone isn’t going to fall out of the sky in the supermarket car park, or on the dairy aisle, or between your car and your front door, and while you might meet someone at the gym or at work, you’re not being proactive enough. You’re just hoping fate bites you in the bum without you having to get uncomfortable.

25. Dating requires effort. Sometimes you’ll have to drag yourself out when all you feel like is curling up in a ball and going to sleep. Yes the date might not end up being that great, but by the same token, it may well be. Showing up is a big part of living.

26. Dating requires resilience. You are worth it. It’s not easy out there today and too many people seem to think they have too much choice causing them to behave as if everyone is dispensable. Nonetheless you will have to work on keeping the faith even though some days, weeks, or even months will be more wearying than others.

27. Do not expect from people what you are not capable of being and doing yourself. Anything that you’re expecting from dates are things that you yourself should possess. This will stop you from looking to others to fill voids.

28. Don’t do ‘The Reach’ on dates which is where you offer to pay and make like you’re reaching for your wallet/purse but have no genuine intentions of paying. It’s very insincere behaviour made even worse if you are going to judge the other party if they accept your offer. If you don’t believe in paying on the first date, don’t reach.

29. The only way you can discover if someone shares the same values as you is by spending the time and getting to know them. What do they believe in? What are their plans and their goals? What’s important to them? Ask questions, listen and even more importantly, pay attention to see if they’re living in line with their values.

30. Remember those people who are rude to staff or even you on dates? They’re an obnoxious person to date as well.

31. When you go on that first, second, or third date, just focus on experiencing the date. Be mindful. There is no need to be putting your name with their surname, imagining them on holiday, trying to work out if you can marry them, and basically galloping too far into the future.

32. Of course once you are dating someone, be careful of anyone who is afraid to even think ahead to the following day. It’s OK to make some plans. You don’t need a Future Faker or somebody who is future avoidant.

33. Don’t be too quick to write somebody off especially if you tend to judge books by their cover or are inclined to judge based on whether you get ‘sparks’. Unless something disastrous happens or it’s very tense on the date, the likelihood is that while some of you may hit it off on the first date, it often takes two or three dates to get a sense of whether you’re really interested and to even form an initial impression of who someone is.

34. But be careful of trying to ‘force’ you to like someone just because you think that you ‘should’. Someone could be The Nicest Person In The Universe TM but if you have little in common on both the interests and core values front, that is OK. You don’t have to be with someone just because you think they’re really nice. They don’t need your pity and it can come across as condescending. They also deserve somebody who appreciates them for who they are and isn’t just with them because they think that they’ve stumbled across a ‘rare species’ – a decent person.

35. Be careful of anyone who is reliant on texts, instant messenger, and email as their dominant forms of contact as these are forms of lazy communication that not only lead to a lazy relationship but may cause you to build sandcastles in the sky. Make sure that there is plenty of human-to-human contact and that you’re not predominantly relying on words.

36. Am I able to be myself and love and live with my boundaries? You need to have a positive answer to this question if you’re thinking about going from dating to being in a relationship with someone. People respect boundaries even though we as individuals are often afraid of setting and living by our boundaries for fear of rejection, however, people respect those that know their own mind, have personal security, and aren’t afraid to say no. The people who are reliant on dating you without boundaries will of course walk away but that’s OK because you don’t want them anyway.

37. Is what I want from this relationship what this person is actually capable of giving, not based on who I think they are, or who I’d like them to be, but based on who they consistently are now? When you’re further along in dating and are thinking that you want more, this is a question you must be able to answer before you commit.

38. If you feel most attracted to people who are not interested in you and typically increase your disinterest if they are interested in you, take this as a warning sign that something is very wrong. Basically if you only want people who are not interested in you, you have to ask what type of people you’re interested in and why you only want people who don’t share your interest because it indicates a pattern of being triggered into feeling interested when you on some level sense or even know that it’s not going to be reciprocated. You value attention that you have to fight and perform for. There will be a habit of seeking validation and getting trapped in feelings of rejection. This doesn’t mean you’re interested – it means you want to be right and chosen and ultimately you cannot keep your self-esteem and chase after disinterested parties at the same time. Our relationships give us a window into understanding ourselves. Whatever it is that you’re looking for from these people is what you need to work on within you. You will also find that if you do some work on healing any childhood issues and/or traumas that contribute to this pattern that you will stop being ‘activated’ into unhealthy dynamics.

39. Introduce him/her to your family (and friends) gradually and when you have got a real sense of whether you like and know them. I would be cautious, for instance, about introducing someone to your kids until you’ve established that you are actually dating and that they’re trustworthy.

40. There is a time and a place for talking about past relationships but be careful of who you share this information with. There is such a thing as too soon but also if you’re with a dubious person they will not only use the information that you tell them to draw negative conclusions about you but they may also adapt their behaviour to suit the information that you share which will cause them to end up portraying themselves in a false light. I’m not saying don’t share information but what I am saying is be authentic in your reasons for sharing the information and don’t overshare.

41. When you do get to talking about your past, it’s about striking a balance. The key is that you shouldn’t be emotionally invested. If you come across too cold, you may give the impression that you’re trying to pretend you’re not into them and obviously mouthing off about them will make the other person really uncomfortable even if they don’t show it. You need to be in neutral territory. I have found that it is a lot easier to have these conversations when you have got to know each other and you know enough about each other not to feel daunted by the conversation. We all have baggage and we all have a past. If you’re not judging you for anything that you’re sharing and are in fact at a much better place about them, they cannot use it against you plus you won’t project your own feelings about what you’re sharing onto them.

42. Don’t go to the movies on the first couple of dates. It is important that you are both communicating and you can’t do this if you’re sitting in the dark watching a film. Whatever your choice of date, ensure that involves a high level of interaction. If you do go to the cinema, make sure you do something before or after.

43. Pay attention. One of the biggest causes of dating and relationship issues is failing to pay attention to obvious code red behaviour and issues in the early stages of dating which subsequently come back to bite you in the bum when you’re further along in the relationship. You don’t need to play Columbo – you just need to ensure that you are aware and alert.

44. Don’t invite them back to your place or go back to theirs on the first few dates. Unless you happen to know them very well before a first date, I would strongly caution you against going to their home for a date simply for safety reasons. Aside from this, the whole going to theirs or your home just puts you a hop, skip, and a jump away from the bedroom and just makes it easier to create an awkward situation. It’s best to avoid temptation especially if you are prone to getting sexual very quickly. It’s also better to be on neutral territory.

45. If you’re interested, don’t pretend you’re not interested. Not only is this childish game playing, but you will totally convey the wrong messages about yourself. You may think it’s a way of trying to get them to prove their worth but this is the type of games that I see people come up against with Mr and Miss Unavailables as well as assclowns, so don’t perpetuate bad behaviour that you wouldn’t like to be on the receiving end of. You also need to be careful of playing games because some people will get off on the chase, build you up and then discard you. You will also struggle to decipher whether they are also playing games so it just basically puts you on the wrong footing.

46. If you’re interested say so or even better, show that you’re interested. This doesn’t mean sex by the way but it is as simple as saying that you’ve really enjoyed yourself and their company. This isn’t a big deal and doesn’t mean that you’ve ‘showed your hand’ but it leaves them with no reason to think that you would not be interested in another date. Dates can often be fraught with underlying anxiety and confusion stemming from miscommunication. Remember that what one person terms as showing interest is not what another may see it as hence being ambiguous isn’t helpful.

47. People do sometimes pretend to be more than what they are, but will always struggle to maintain a complete facade on all dates. You will only notice this difference if you are not in Lala land with rose tinted glasses and the fur coat of denial. If you’re showing up as and being yourself on dates, you will have no problems deciphering whether you’re around someone who is a bullshitter because you have a sense of consistency and authenticity. If you’re pretending to be something that you’re not then all it does is muddy the waters especially because you will know that you’re not being honest so won’t be able to figure out whether it’s you or them.

48. Put your mobile/cell phone on silent or vibrate! Don’t take calls or text throughout the date. Go to the bathroom. But obviously don’t spend most of the date sneakily taking calls, texting, tweeting or whatever. It’s really bad manners. Be in the present.

49. Listen don’t just talk on dates. People think that you need to talk a lot for good communication but there needs to be a balance between talking and listening. If you’re doing most of the talking, something’s not right. And yes, sometimes this is down to nerves but slow down a little to get a sense of whether you’re overcompensating for the other party or whether you listen too much to your own talk and project this onto the other party. If you’re already thinking about what you’re going to say next, you’re not fully engaged and if you’re not aware of what you’re doing, you may make assumptions about your date based on how much you enjoyed talking as opposed to the actual date.

50. Get your head in order before you date because we end up in relationships with people that reflect what we believe, so it’s best to make your beliefs and attitude positive. Don’t date if you feel cynical, jaded, or bored with dating because it will manifest itself in your behaviour and choices. You will be biased to look for evidence that supports your mindset. Check out The Get Out Of Stuck 21-Day email series.

51. If you are unsure about someone or there is key information that you still need to know about them, do not sleep with them. Trust me, shagging them isn’t going to clear up the information gap! Listen to you. Give you time to decipher what you’re feeling, thinking and experiencing.

52. Talk positively about you when you’re on dates. Do not sell yourself short. Don’t shoot down compliments or run you down. Just say thank you when complimented. Speak about you with love, care, trust, and respect. If you can’t see why someone should date or love you, how can they see it?

53. On your dating profile, if you’re only interested in people who are looking for a serious relationship, say so. Often people say they are looking for a mix of things and get a mix of people, but it pays to be very specific in your profile because even though you may get less respondents, you are more likely to weed out people who are just looking to get laid or to clock up dating numbers, and even if you do still find yourself with one of these people, knowing that you have been specific means that you can let them go because you were upfront. If you don’t like ambiguity, don’t be ambiguous. If your relationship values and your needs and desire are to be in a long-term relationship, all that a casual relationship is going to do is take you on a detour and get you laid.

54. Always tell someone that you’re going on a date. It’s good to be safe! If they seem weird, listen to your gut. Meet in an open, public place for the first few dates and keep your spidey senses alert for anything that comes across as strange, intense, or stalkery.

55. If they come with excess baggage that involves a current partner, tell them to jog on. Or tell them to come back when they’re baggage free. Keep note though – it’s not a good indicator when a person is still dating and shopping around despite the fact that they’re in another relationship! If this doesn’t reflect your own values, all that being involved will do is erode your self-esteem.

56. Don’t discover a piece of information about their ex and then try to make yourself into them or start to feel insecure. If their ex is so amazing, they’d still be there so all you’re doing is offloading you to try and play someone from the past. You’re taking information out of context and you’re not valuing the beauty and essence of who you are. Imitating someone that they’ve broken up with is a one-way track to pain and loss of self. You’re not a replacement; you’re you.

57. Don’t allow people you are dating to call you up after the whole week has gone by and expect you to make plans. This means that they shouldn’t be calling you up on 5pm on a Friday after radio silence or sporadic lazy contact expecting you to be free, and you shouldn’t be accepting their invitation. It’s called you being too available and them being too lazy to deem you important enough to make plans with. Value your time. Don’t wait around or put your life on hold so that you can be ready to drop everything should they call. Set the tone because when you don’t drop everything, they will learn that they need to ask in advance or move along if they don’t want to step up.

58. Stay positive for the second and subsequent dates and be careful of creating oversized expectations. If the first date went well, this is great, but that doesn’t mean that you should expect fireworks and cymbals clashing for the second date. Manage your expectations and focus on getting to know them. On the other hand, don’t go in with a negative attitude which assumes that your date is bound to screw up because it’s what you expect from all second dates. Easiest thing is to to go into the date rooted in the present and showing up to enjoy yourself. Let the date chips fall where they may.

59. Judge people on the merits of their own actions. Don’t tar everyone with the same brush because you’re afraid of trusting yourself. In fact, you’d better learn to trust yourself before you start dating otherwise you will either be too fearful and find any reason to find fault, or you will love and trust blindly, which is dangerous also.

60. Don’t be bitchy, aloof, confrontational, or aggressive. You may think you come across as independent and self-assured but actually you’re coming across as bitchy, aloof, confrontational, or aggressive. They don’t exactly scream ‘date me’. Make sure that how you intend to come across is how you come across. Communication is only as good as the message that’s received on the other end. This goes back to point #46 – You may see your wisecracking and poking fun as your way of being playful and showing that you like them but if what you’re wisecracking about hits a sore spot, they may think the opposite. It’s not about pretending to be something that you’re not; it’s about being self-aware. When we are, it means we’re empathetic and in reality about who we are and why we do certain things.

61. If the person is reluctant to say where they live or talk about their living arrangements, be warned – they’re likely to be very shady. You would be amazed at how many people I hear from that have been with somebody for months or years who they don’t know where they live. That’s just not healthy. They don’t have to give you their exact address when you don’t know each other – safety first and all that jazz – but if they’re sketchy about their living arrangements, that’s a code amber alert at best.

62. If you only see and hear from them late at night, it’s not because they’re very busy with their job or that you’re the last voice they want to hear before they go to sleep – it’s because you’re a booty call. Booty calls and self-esteem don’t go hand in hand, especially when they’ve been going on for some time.

63. Learn to say ‘NO’. Much of the drama that happens with dating arises from not being true to yourself and being agreeable. It comes from fear and guilt around your right to say and show no. No is how you communicate your limit and your line. Nothing good comes from being a people pleaser.

64. If you expect honesty, be honest on your dates. That doesn’t mean being rude – it means being yourself with respect. It also means being willing to step up for you and make an exit when it becomes apparent that they are not honest.

65. Guys that like you SAY and ACT like they like you. Same goes for women. If the two things don’t match up consistently then you know that this person is a blow hot and cold’er.

66. Avoid the dating equivalent of premature ejaculation. Don’t be premature with your conversational topics. You don’t need to know if they see a possibility of getting married or having kids, or even having a relationship with you on the first date. In fact, it takes time to discover these things and before you can even contemplate doing any of these things with anyone, you need to get to know them first.

67. If you’re unsure after the first date, that’s OK. Go on a second and third date. Seriously, there is no fire. Some people take a bit of time to warm up and that’s OK too. Remember – we have often dated people with whom we felt instant rapport who have turned out to be no good for us. It will do you no harm to slow your roll because we don’t always judge people fairly.

68. Don’t date because you feel pressured by your family and friends. They’re only projecting their insecurities on to you or not realising how they are coming across. Date because you want to.

69. Make an effort with your appearance and attitude on your date. Put your best foot forward. Not only will it create an impression but it will positively affect your mindset.

70. Work out what you genuinely want from dating. Are you looking for a relationship? Are you looking to get laid? Are you looking to pass time? There are people out there to suit whatever you are looking for but it’s important to know what that is before you start so that you don’t waste someone else’s time or have them waste yours. If you are looking for the latter two, adjust your expectations accordingly and be careful of changing the goalposts and your expectations if the person was wanting the same thing that you originally were.

71. There’s no such thing as ‘out of your league.’ Be careful of letting your own perception of your self-worth skew what you believe that you’re deserving of. People who don’t feel that they’re good enough tend to be with unhealthy relationship partners as a way of validating their beliefs. If you feel that you can’t or ‘shouldn’t go for certain people, have an honest conversation with you about your beliefs and address the source of your self-esteem issues.

72. Can a booty call grow into dating grow into a relationship? NO. You’re not in the film, Friends With Benefits. This is real life.

73. It’s more than OK to have drinks on your dates but if you get drunk and lose control of yourself, it may be best to leave out alcohol or limit yourself. That’s a basic lesson in boundaries, self-discipline and self-awareness. Look out for you.

74. Spend your time in the present. Your dating experiences change when you’re not living in the past and anxious about it and also when you’re not trying to predict the future and getting anxious from forecasting doom.

75. Be careful of Defining The Relationship Talks. Of course these DTRs can be useful but I tend to find that people use these in the absence of judgment and either jump the gun and have the talk too soon or they leave it until it’s far too late. Or, they have DTRs all the time and this becomes how you both communicate and that’s not good either. If you’re still defining the relationship, it means it’s undefined and that you didn’t like the conclusion of the previous discussion!

77. Don’t dissect the date itself or the person on the actual date. Save the blow by blow analysis of the person and the date for when you get home and speak to your friends. You wouldn’t appreciate being critiqued. Unless they have done something really rude that you can’t avoid mentioning, don’t put yourself or them through the uncomfortable act of you telling them all about themselves.

76. The purpose of having Defining The Relationship (DTR) talks is for you both to state and be clear about what type of relationship/dating situation you have. It should remove ambiguity and you should both understand if there are any limits to your expectations of that person and the resulting relationship that you have with them. You shouldn’t need or have to define the relationship very often. It’s clarification that you’re exclusive and that whatever it is that you’re both doing, you’re clear and in agreement about what that is. Do not assume!

77. Don’t try to control the uncontrollable. If you have a habit of struggling to allow people to unfold, it’s because you’re trying to be in control of the outcome. This can put a great deal of pressure on both you and the relationship. If you find that you’re also trying to micromanage their personality and behaviour because you’re worried that if you don’t, the relationship will flounder, you also need to step back. What are you worried about? Which insecurities is your date tapping on? You’re the only person who you can have significant influence and control over the feelings and behaviour of.

78. Have a life. You’ve met someone – does that mean you roll over and stop having your own life? Don’t fall into the trap of sacrificing your own life, neglecting friends, family or even work just because you’ve met someone and are getting a bit of action. If you typically abandon everything and everyone once you’re in a relationship, slow your roll and force you to make time for your life. Healthy relationships need interdependence which is where you are each independent entities with your own life who have a mutual healthy dependency in the sense of being connected to and in the relationship. This is entirely different to being codependent, which is where you are excessively emotionally reliant.

79. Acknowledge and confront any code red and amber issues. Trust me when I say that the things that you fight about or eventually break up over are often things that could have easily been found out in the early stages of the relationship if only you’d opened your eyes and taken off the rose tinted glasses. Rather than play happy honeymoon all the time, don’t be afraid to call him on behaviour that you’re not comfortable with as you need to know if he is worth your energy.

80. No phone or online sex with people that you don’t know. If someone that you met online this morning is already sending you penis shots or trying to get you to talk dirty, you can trust me when I say that nothing more than some sexual flirtation and possibly a wet screen or seat, is going to come of this. The worse thing is that even though they invite you to participate, these people often mark you down for participating. Unless having sex with strangers is your ‘thang’, don’t engage in inappropriate sexual flirtations or virtual/phone sex with people that you don’t know.

81. Don’t hang around with people who have negative attitudes towards dating, especially if they affect your mindset and cloud your judgement. This is both your single and attached friends. It’s good to spend time around positive people who support you as opposed to negative people who suck the fun out of things, undermine your choices, trigger you questioning yourself, or portray you and your life as doom and gloom. It’s very patronising when attached people make out as if you’re something to be pitied and just as much of a headwreck when single and disillusioned friends try to sh*t on your efforts. Their experience is not your experience plus your story isn’t written yet.

82. Learn to feel good about yourself so that you act in accordance with how you feel. Treat you well, be considerate of the thoughts that you feed you and make sure that what you profess to believe and want is reflected in your actions and attitude. Read my 100 tips on self-esteem.

83. Find out who you are, what you like, what your interests are and what your goals are, and then find events, clubs, places etc that not only reflect these but give you the opportunity to meet like-minded people. It doesn’t matter if it turns out that you don’t enjoy something – try something else. Don’t make umpteen excuses as to why it’s not worth your while to do something because all the excuses boil down to is trying to avoid change and getting out of your comfort zone. Meetup.com has yielded great success for many BR readers and make sure you check all of your local websites and resources. Be open-minded as you will be surprised at what you will enjoy while trying out new things. It also gives you an opportunity to practice your social skills.

84. You will not meet people on your sofa or burying yourself in the illusionary world of the internet. Get out of the house and don’t kid yourself about your efforts to meet people if you’re not getting out of your social comfort zone.

85. It’s good to have a dating hiatus especially if you’ve found that dating is making you miserable, cynical, or yielding a familiar pattern that isn’t working for you. Taking a 3-6 month break lets you focus on you and when you come back to it, you can start afresh with renewed vigour and attitude. Obviously avoid repeating the past – relationship insanity. This is carrying the same baggage, beliefs, attitudes and behaviours, choosing the same people different package and expecting different results.

86. Take a sex hiatus if your sexual interactions are clouding your judgement and/or yielding negative results. Dating without sex can be wonderfully liberating. You will quickly weed out people who are just out for the chase and looking to get laid and you can focus on getting to know your dates in reality and discovering common values.

87. Don’t treat your dates like armchair psychologists and don’t allow you to be treated in this way. Totally.Not.Appropriate. You (or they) will convey all of the wrong things about yourself and you will communicate ‘I have problems. I am not personally secure.’ It’s very draining to be in a dump and charge up situation.

88. Unless you are in a relationship, you trust them, and there is a healthy foundation to your relationship, no lending to or borrowing money from dates. If you lend it, consider it gone! If you borrow it, pay it back asap. Romance and finance don’t mix!

89. Don’t play games. Games really shouldn’t enter into the dating and relationship arena unless they’re in the bedroom. Playing games creates unnecessary drama by manipulating people and the outcome of situations. You may feel like you need to test your dates but you’re creating a relationship based on misconceptions. And how can you trust what you think you know when you’ve been playing games? You don’t want to give the impression that you’re childish or get suckered into relationships that are really about vying for power. This will render your relationship unworkable.

90. Don’t go for the low hanging fruit, easy options because you may find that you’re dating people who you really need to stop wasting your time, energy and emotions with. Basically if you date with self-esteem and a positive attitude, you won’t feel the need or desire to date or continue dating people who are inappropriate or whom you’ve specifically chosen because they’re ‘easier’. The typical reason why people do this is because they think they’re unworthy and also because they think that by dating ‘down’, that the person won’t want to leave. Resolve your Florence Nightingale and Fixer Upper tendencies and raise your standards.

91. Don’t try to buy or shag your way into someone liking you. One could potentially leave your wallet empty and the other could leave you emotionally empty. Convincing isn’t sexy. The more you try to convince and perform is actually the more questions you raise about you. You are worth a lot more than this so don’t sell you down the river.

92. Start as you mean to go on. Be personally secure, have boundaries, treat you with love, care, trust, and respect and live by your values because being yourself is what makes you attractive to the other person and it also gives them a birds eye view into what you will be like in a relationship. Mistreating you or pretending to be somebody that you’re not doesn’t scream commitment candidate and wearing a mask significantly diminishes your self-esteem.

93. Be careful of multiple dating. It’s a tricky business juggling several people and requires you to be very organised and detached. See #94 Unless you’re anal retentive enough to do the juggling without breaking a sweat, steer clear. Dating is a less stressful when you’re not cacking yourself about mixing up names or worrying about sending an email or text to the wrong person.

94. Multiple dating, emotional unavailability and commitment-resistance go hand in hand. You cannot be emotionally available to all of these people. This is fine when you and they know the score but it’s not when you are detached from your actions and are actually dating multiple people as a way of not letting protecting you from intimacy and vulnerability. I’m not suggesting that you have to be ‘exclusive’ as soon as you go on one date with a person but if you are dating several people at once on an ongoing basis, it’s time to have an honest conversation with yourself.

95. Don’t date other people with a view to making the one you want jealous. The fact that you or someone can be jealous is not a sign of love – it is a sign of control. You also cannot keep up the ambiguity and jealousy on a medium- to long-term basis – it would be exhausting! That and it’s playing games. If you have to make someone jealous for them to feel like they want you, they’re not worth dating. As an aside, Mr/Miss Unavailables get interested when they’re in danger of losing you and then when they feel secure of your affections…lose interest. In life you will find that a lot of things change when you come from a place of congruency and integrity. How would you feel if someone used you to make another person jealous?

96. While it’s very flattering (sort of) that someone will say that they love you on the first date or very quickly, or tell you that they want to marry you, have babies, move in, they just can’t know enough about you for this to be sincere. People who try to Fast Forward the relationship from the get go often rush you through the early stages so that you miss vital signs that all is not well. However, the red flag is the fact that they’re speeding you through instead of letting the dates and the subsequent relationship grow at its own pace.

97. Don’t date out of desperation because you end up with desperate dates that you end up doing a Fixer Upper or suffering with ‘I Can Change Him/Her’ syndrome. If you date from an unhappy place when you already have low self-esteem, you will invite people into your life that reduce your self-esteem even further and cater to the insecurities that you already feel. When you treat and regard you with love, care, trust, and respect, you will not accept less than what you can already be and do for yourself from someone else.

98. You don’t have to say ‘I love you’. I’m not saying that people don’t mean it when they say it but often these three words get uttered because people want to move the relationship to where they think it should be. Remember that while you may think you mean it, it’s best to only say these words when you have all of the building blocks in place for a  relationship. Saying these three words to someone who for instance, struggles to remember to call you, is a recipe for disaster. Anything you say or do, do it because it’s who you are not because you’re trying to engineer something out of the other party.

99. Avoid emotionally unavailable men and women (Mr and Miss Unavailables) as well as assclowns (unavailable as well being shady users and abusers) like the plague. They may seem exciting and dramatic at first but you won’t be saying that when they’ve screwed with your head and you no longer know your ass from your elbow.

100. Enjoy dating and don’t take it or yourself too seriously. This means striking a balance between meeting people, socialising, and the potential of finding a relationship. Not every person can be ‘The One’. Not every date has the potential to turn into a relationship. Not every date should turn into a relationship and if it did, you’re either ‘lucky’ or you have your quality control filter turned off. It’s okay to want a relationship but don’t make it the source of your self-esteem.

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