I get so many emails asking me about whether to date someone who is separated, recently divorced, or even fresh out of a breakup that I wanted to tackle this tricky subject. We’re often scared (even if nothing has actually happened yet with a particular person) that we may be letting our last chance or even best chance saloon slip away. We may be imagining all sorts of problems that may or may not exist or we’re rationalising our own boundaries, values, and even prior experiences of being in one of these situations (so knowing that we may struggle with the emotional consequences) and are thinking along the lines of, ‘Well… I’m of a certain age so I need to prepare myself for turning a blind eye to any code amber / red actions and indications because people in this age group tend to be recently broken up / separated / divorced‘. OK….

There’s no easy answer to the question of what the ‘right time’ is for dating a separated or recently divorced person. What you have to keep in mind is that separated is still married until the divorce is finalised and that means that there’s likely to be emotional as well as legal ties.

It would be handy if we could avoid the vulnerability that comes with doing the due diligence and taking appropriate action where needed. What we forget is that even if a person hasn’t just exited a relationship, aside from knowing our own boundaries (which can rule out certain things that we’ve already made a decision on in advance of), we cannot get all of the answers upfront or have someone tell us what ‘the ending’ will be.

Each situation is different but what you can say with a high degree of certainty is that someone who’s just fallen out of their marriage, who’s still in reconciliation negotiations, who’s still very influenced by their spouse, and who has been separated for a long time ‘just because’, is going to bring pain into your life. Same goes for someone who’s not over their divorce and has beliefs that affect their ability to be committed.

I personally know people who have gotten together while one party was separated, and in one case the wife refused to sign so they had to wait for it to lapse and got married as soon as it did a few years later, and in the other instances where it worked out, there was no faffing about with the divorce, Future Faking etc. In the situations where it didn’t work, the separated party overestimated their readiness and actually, part of the reason they dated had been to avoid their feelings about the demise of their marriage.

Avoid falling into the trap of not seeing the wood for the trees: There are people left brokenhearted due to being involved with partners who were still affected by a breakup or divorce that happened anything from months to decades before.

We can take the period of time since the breakup into account but we also need to note whether actions matching words are amounting to somebody who is available for a mutual, consistent, balanced (no pedestals / controlling), progressing relationship that can blossom into increasing intimacy and commitment. That’s what we need to look for. It’s very easy to look at a person’s age, background, what they earn, their relationship history, their appearance, their divorce, and whatever else we’re focusing on, and rule them in or out on this basis, but in the end, regardless of any of these things, we still have to assess our own boundaries and do the due diligence.

It’s not about judging a person for being separated or divorced – it’s about judging the overall situation and working out whether it fits with who we are and where we’re headed.

The experience over time that we spend with a person means that we get to see if actions and words match and whether what we thought or they suggested was on the cards is actually happening. Yes it’s a ‘risk’ but it’s little more risk than in any other dating situation. That said, keep in mind the following:

1. Don’t assume that because you’re being pursued or that there’s certain future talk that it ‘must’ mean that they’re over their ex and ready for a relationship. 

2. Definitely don’t assume that because they’re separated or divorced that have a PhD in commitment or that you’ll get the same. All it means is that they’ve been married. And that it ended.

3. If you typically struggle with the uncertainty that comes with being with somebody who still has their previous relationship to resolve, or you know based on experience that you’ve had your fingers burned by being involved with separated or recently broken up people, don’t go there. A person cannot promise not to hurt you or that their marriage breaking up isn’t going to affect you hence if the possibility of either of these happening sends fear ripping through you, know your own boundaries instead of playing the breakup slot machine again.

4. ‘Recent’ is of course subjective but it’s safe to say that if you become involved with someone who is weeks or even days out of their prior relationship, you’re gonna get some blowback. You remember what it’s like in those first few days, weeks and even months depending on how long the relationship went on for – you may still have been in touch, arguing, negotiating, or even hooking up. Is this what you want to be in the middle of? You can of course chance your arm but then you have to back away when it becomes clear that the ex files haven’t been closed.

5. If you’ve already determined your boundary on this issue, don’t bust it, live it. I know of quite a few people who were told to wait and come back when they’d had some more time/got divorced. Now of course, a person who is avoiding their feelings will just find someone else to avoid them with but somebody who is genuinely interested in you and wants to start off on a good footing won’t mind respecting your wishes – at least they’ll know that they’re pursuing something with you because it’s you they want to be with as opposed to seeking a distraction that’s going to backfire when they realise that they’re unavailable.

6. Don’t project. Most people go through a breakup or few, and it’s not a ‘flaw’ to be separated or divorced hence there’s no reason to go ‘Oooh, they’re separated and I’m a hot mess hence we should be good together’ or ‘They’re divorced and I’m not good enough anyway so who am I to talk?’ Some relationships and marriages don’t work out. Of course some people are separated or even divorced numerous times due to shady behaviour or due to a tad too much Fast Forwarding but that’s stuff you’ll find out through due diligence, possibly quite quickly if you have your feet on the ground and are listening and watching. Judge who they are on the merit of who they are. I know of somebody who is getting married for the fifth time and is doing their best to hide it from their family including their own children – yeah, clearly they haven’t grown or learned a damn thing from their previous marriages.

7. Don’t enter into an involvement with your emotional airbag inflated. If your interest tends to get piqued by being a ‘buffer’ to someone who is transitioning, it would be more beneficial to evaluate why this is attractive to you. You camouflaging their issues is only causing you to blend into the background of your own life. If you’ve typically been a Fallback option, it’s best to steer clear of these situations unless you’re absolutely certain that whatever contributed to your previous habits has now changed.

In the end, it’s about growth because a person can have gone through a number of dubious relationship experiences and then gone through a period of personal growth and their current and future behaviour reflects their healthier habits of thinking and behaviour. These will be self-evident – you won’t need to pull out your magnifying glass, start making things up or coming up with rationalisations.

Your thoughts?