questionI’ve had a lot of emails and comments over the past few days regarding what questions you should be asking boyfriends etc. Putting aside the concern that you don’t know what to ask, the simple answer to that question is this:

I can’t tell you all the questions that you need to be asking in your relationship because every relationship is different. There are of course, basic things that you should know, but after that, questioning people you’re involved with boils down to:

1) Clarifying information that they have shared with you.

2) Filling in gaps in knowledge where there are question marks in your relationship.

3) Finding out what you want to know.

Any and all questions you ask in your relationship, should answer the following key questions for you:

Do we share common primary values? [This means you need to know what is important to you and ensure that they are of prime importance to them]

Am I able to be myself and love and live with my boundaries? [Generally, you can tell this through their actions and your reactions. Also if them saying or doing something changes this ability – it’s a red flag]

Do I love, care, trust, and respect this person and am I able to act with love, care, trust, and respect towards myself? [Ditto]

Have I learned information about this person that has me hoping he will change? [Any information you have found out, have you accepted the information? Or have you rejected it and replaced it with hopes of change(Florence Nightingale and control issues)? No amount of questioning will get that hope confirmed – accept as is and decide if you can exist in the relationship with them.]

Do I like how he/she treats others? [Find out about his friendships, colleagues, family, exes – don’t interrogate. You should find out this information because you witness it or it comes up in conversation, however if it doesn’t – ask.]

Do I enjoy my relationship with this person? [Only you can answer this question]

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? [If it’s no, you’ve got issues]

Do I feel safe with this person? [The answer to this lies in listening to yourself, the answers that they give, and the experiences that you have with them and factoring it all in to the big picture of your relationship.]

Why do I want to be in this relationship? [Only you can answer this question ]

If you are not able to answer these questions or the answers throw up red flags, you either need to ask more questions and get the clarification and answers you need, or it’s time to get out.

If you don’t know them well enough to know the answer to these questions because you are dating, this is what dating is for – the discovery and fact finding phase.

It’s all very well finding out his favourite colour, your shared interests, how great he is in bed, or how much ‘chemistry’ you think you both have, but do not make assumptions based off secondary values and assume that everything else will correlate.

Before you decide that you commit yourself, make sure you know the answer to these questions because if you commit before, you will love and trust blindly without basis.

Clarifying, filling in gaps of information, and getting answers comes down to reframing something that they tell you and inserting a question, asking what something means, and taking the piece of information you want to know, and asking them. That and using your powers of observation and awareness of red flags, boundaries, and values to judge the situation and their actions.

Reframing: Assclowns and Mr Unavailables do like to get all airy fairy, vague, high level, and obtuse. They end up running rings around you and you forget what the hell you and they are talking about.

To ensure that they don’t dodge you or accuse you of making things up, don’t say ‘What do you mean by that?’. Instead say: What do you mean by [insert what they just said]?

Take something they say that is questionable or requires more clarification and reframe it as a question.

You ask: I need to know where I stand – Are you ready to be in a committed relationship with me?

He says: Well….you know I’m busy with work…and you know I’ve got all of this stuff to sort out with the house…You know I like you a lot…I’ve just got a lot on…I’m just not sure where I am right now. Can’t we just stay as we are?

You ask: OK, but what does that mean? You say you’re busy with work, the house etc – what does that mean to our relationship? Are you telling me that you are too busy with your stuff for the relationship? What do you mean by you’re not sure where you are right now?

That’s not jumping to conclusions; that’s taking something that they’ve said as a way to vaguely answer you and asking them to clarify instead of sitting on the fence keeping you in limbo land.

Be careful of parroting and people that tell you stuff to get you off their back. All the ‘me too’; uh huh’;’I agree’ is dangerous especially if you already know that they tend to go back on their word and mean something different.

Don’t be afraid to repeat what you’ve just said and say ‘So you agree that we should X/Y/Z?’

If you don’t know information that is important enough for you to be burning up brainpower over and you’re not able to figure it out through actions and knowledge you possess about red flags, values, and boundaries, ask. Yes it really is that simple.

What did you mean when you said […]?

When I saw you […] what was going on there?

When we talked about […] you said […] but that hasn’t happened yet/you’ve done […] instead. Can you tell me what is actually happening? (Or…do you no longer want to […]?)

You said that you wanted to go out on Saturday when we spoke earlier in the week but I didn’t hear from you. What happened?

I haven’t heard from you in six months – why are you calling?

You’ve just broken up with your wife – do you really believe you are ready to start a relationship with me? I am looking for a serious relationship. If we get into this, I need to be sure that you understand what you’re getting into?

OK, I have just told you that I want […] [….] and […]. Are you saying that you can give me […] [….] and […] ?

OK, you say that you’ve missed me, that you love me, made a mistake, and couldn’t take it when I ignored your calls and texts. Are you telling me that you want to get back together with me? Do you understand that if I take you back, I’m expecting the […] [….] and […] that you promised me?

You asked me if you could borrow £X because you had […] problem and you told me you would pay me back by […] but now it’s […]. I appreciate that things change but I need to know when you will be able to pay me back?

You said you would finish it with her. Have you told her that the relationship is over and that we are now officially together?

Have you taken your profile off […] site and […] site and […] site?

Aside from this, there are basic questions:

Where do you live? (Or where do you live most of the time? Are you based in this city/town?) Not everybody is straight up about this information. Make sure they’re in your area and not long distance (unless you want it that way), that they aren’t still living with their mother/ex/wife etc or only living their one day a week because they’re always travelling with work. What type of work do you do?/Do you work long hours? What type of stuff do you do in your free time?

All of these questions give you a sense of the type of life that this person is leading.

Are they a nomad? Are they cagey? Are they a rolling stone gathering no moss on a variety of women’s beds? Are they bill dodgers? Are they looking for a woman to bankroll them? Are they still attached to their mother’s umbilical cord? Are they a totally normal guy? Yay!

How long have you been dating? Have you been single for long? If they’re relatively normal, this should open up a humorous conversation or it may reveal clues to whether you need to be worried or bailing. Also try – Do you enjoy dating? Not likely to answer with a ‘yes’ or ‘no’ and instead likely to open up.

When did your last relationship end? (Ask after the third date or third detailed/lengthy contact) I have a strong piece of advice that I give to anyone dating – do not talk about exes on the first three dates. After that, do ask questions and be wary of 1) the amount of time since it ended or 2) if they become very negative or emotional, or 3) they’re reluctant to discuss. Do not change yourself to try to suit information that you have heard from the questions!

Why did your last relationship end? Normal people have no problem talking about the fact that their previous relationship ended. The people that do, are the people that don’t want to give you a window into how they may treat you. This isn’t just about what they say, it’s what they don’t say and also how they react. It’s not for you to judge him based on his previous relationship but your spidey senses should be working overtime if the same issues crop up in your own relationship.

Does he come across nervous or agitated? Does he become aggressive? Does he shut down? Does he withdraw from you afterwards? – this is a subtle communication of the message that asking questions will be punished with withdrawal so you will be hesitant about asking questions next time. Does he slag her off? Be careful of joining in or being smug – it could be you some day. Be wary of guys that call their exes psychos – more often than not, this is a total exaggeration and a major red flag.

These questions give you a sense of the type of relationship integrity (if any) that they possess.

If he’s separated – When did the separation start? Have divorce proceedings started? Work out if they’re actually getting divorced or just on a break and if it’s very recent, or they’re reluctant to be definitive about when they separated, be very wary. If it’s not solid, I would be extremely cautious because more women get caught out by separated men than don’t – walking baggage knee-jerking to new relationship. Oh and they’re still married. Let me say it again – he’s still married.

Do you have children? This isn’t because children pose a problem but more that if he does have children, it does reveal an aspect of his life that he’ll need to open up on if he’s looking to continue seeing you. If he doesn’t see them, why not? If he becomes negative, be nervous. If he starts speaking about their mother in a derogatory manner, also be very cautious. As a word of caution to those who suspect they’re involved with an assclown, it’s not a bad idea to get clarification on how many kids and with who? I know women involved with assclowns who have four kids by four different women who they don’t support and yet most of these women have gone on to have a child who also isn’t supported. If a man is ducking out on his responsibility of taking care of his children and is pretty shameless about it too, it’s better to know now and use that information to beat a hasty retreat.

Other questions when you’re further down the line…

Are we exclusive? It’s best to know if you’re one of many as you can opt out or adjust your expectations. Don’t ask this on the first few dates….

Are you sleeping with/dating other people? Do not put yourself at risk. Both of you have a responsibility to be honest with each other. From the moment you’re contemplating/discussing having sex or already pulling each others clothes off – ask.

Have you got any STD’s? When was the last time you had a sexual health check? Ditto

Are you ready to be in a committed relationship with me now?

If they say yes: Make sure you discuss what you see a committed relationship as to ensure that you’re both on the same page. What does being in a committed relationship mean to you? – It’s not a crazy question and a relatively normal person shouldn’t struggle to answer this.

There is nothing wrong with asking:

What do you see a committed relationship involving?

Never assume that you both share the same view of a committed relationship. You might think it’s being exclusive, moving in together and having a future. Is he prepared to be faithful? Has he removed his profile off dating sites? Is he still engaging with an ex in a manner that isn’t conducive to your relationship?

Be careful of asking ‘vague’ questions like:

Where do you see this going? Do you want to be with me? This isn’t just a casual thing is it? and other such vague questions. Why? You’ll get a vague answer. If for example, it is a casual thing, he may not want to clue you in on it because it’ll endanger getting laid…. Instead, if you’re being treated casually, it’s safe to deduce that you’re casual.

If they say no: The answer in itself should be enough, but most won’t want to leave it there. You can ask further questions like the whys and hows, but you’ve got the answer – why put yourself through further pain playing chief detective? The topline information is that he’s not ready to be in a relationship. Unless you don’t want a relationship either, you both want different things. Tell him to come back when he is ready.

Have you filed the divorce papers? This is why it’s good to get clarification of their intentions when you get involved with a separated man because they have no reason to not be answering your questions and you have every right to question what is happening.

If not: when do you intend to file the divorce papers? If met with flip flapping – I appreciate that you can’t give a definitive date, but in our last conversation about this you said…

What are your plans for the future? If you’ve been together a while and you’re not in the plans or they’re plans that are out of sync with how you see the relationship, this should ring alarm bells and be an opening to more questions and clarification.

Do you want to have kids/more kids? If you do and they don’t, it’s best to know now.

How do you find out if you share common primary values? Well if you’re unhappy or they’re busting your boundaries and you can’t like, love, respect, or trust yourself with them, it’s safe to say that you don’t share them, but ask questions about your boundaries.

For instance, if you value marriage and security, it’s good to ask if marriage is something that they can see themselves doing. It doesn’t have to be about you if you’ve just started dating. Likewise talking in a general way about work, money, the economy, future plans, should give an idea of their money values, stability etc.

If you ask a question and you don’t get the answer, you need to probe more or ask a different question. Don’t keep asking the same question repeatedly – you’ll get the same answer.
If you ask the same question or variations of it and you don’t hear what you want to hear, it’s because you’re not going to get that answer.

If you ask questions and are met with resistance, vagueness etc, it’s a red flag.If asking questions throws up more questions, it’s saying that either you’re not listening, they’re not answering, or your relationship has too many questions to set sail.

If you ask questions, you get answers, but the actions don’t match, the action is your answer.
Oh and always ask yourself if you can find out the answer through their actions – it’s highly likely that you can.
Your thoughts?


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