Dear Nic and Verity: I'm in my late-30s and was last in a committed relationship three years ago. I have dated since, and focused on enjoying myself, building a life I am very happy in. I also worked on understanding a lot of the "whys" of my own behaviours (in
Ask the experts: How do I give a new relationship the best chance of success?
It sounds like you are already aware that it would not be wise for you to pursue this relationship if he has unclear boundaries with his ex or is emotionally still very churned up. However, you also need to make your own judgment about this, in case he is minimising the work still to be done in his desire to connect with you. The "textbook" approach says that if someone still has a lot to unpack about that relationship's demise, then it is wise for them not to get involved with someone else for a year at least. That time allows space for him to be sure that he has learned all he needs to know about himself from the end of that past relationship before he jumps into a relationship with you.
While it won't feel very romantic, it would be prudent for you to ask a lot of very specific questions exploring how he might still be enmeshed and embroiled in his past relationship, either emotionally or practically. Are there children in common, are all practical and financial matters fully resolved between them? Are they still in contact in any way? What are the boundaries in place? What about with mutual close friends and extended families? Is emotional dependence or closeness still present with his ex? Is he very vulnerable or struggling because he is still feeling a lot of emotional pain or rejection from how the separation occurred? These are all things that are better addressed and solutions put in place before starting a new relationship.
Direct, detailed questions are an excellent way to carry out your due diligence on this new person and their situation. Take care to expect him to engage well with your valid questions and watch for vague or defensive responses and take those as warning signs. You are looking not just at whether he has dealt with the ending of his prior relationship but at his whole attitude and approach to difficult conversations and the vulnerability necessary in intimate relationships.
In that vein, a good line of inquiry is to ask him, in hindsight, what he sees as his contribution to the problems in that past relationship. If someone only blames their partner for everything that went wrong or says something vague like "I know I was also part of it somehow", that is very often a bad sign. It is a noteworthy mark of maturity for someone to be able to self-confront and see their role in the demise of a relationship. It's also a bad sign if they only blame themselves and don't see their partner's contribution to the difficulties in the relationship.
If there are quite a few practical complications to be worked through before he is fully separated from his partner, either emotionally or practically, then we would advise putting this relationship on hold for a while (six months minimum). There are a lot of positives in the mix so far with this man but what screams out at us from what you have written is that there have been only a "couple of dates" and then lockdown. We imagine you have continued to communicate with him during lockdown. Still, we think it is very early days for you to have any confidence in what you know about his personality and style.
At the risk of sounding cynical, it is relatively easy for someone to present their best side on a couple of dates and then with digital communication. We often say that you don't know if someone is solid relationship material until you have a severe disagreement with them or have to challenge them or give them critical feedback. That is when you see how securely or insecurely they respond in these two very uncomfortable types of interactions.
Additionally, we would support Britt Mann's contention that you need to know someone in the flesh to have confidence in your compatibility, which was impossible to do during lockdown.
So, to give yourselves the best chance of success and of avoiding future hurt, we very strongly endorse slowing down after the initial positive rush of excitement (always enjoyable) and thinking more critically and cautiously about the timing for taking your relationship further.
On the other hand, if on questioning it becomes clear the practical and emotional separation is well advanced for your friend, and it is just that he needs a little more time for reflection and recovery, then you could go slowly and date and not get too deep into the relationship.
However, lust and limerence make it hard to go slow. Ditto if you are feeling desperate for a companion or time pressure to have kids etc. If you go down this path, then setting some clear parameters may be necessary to prevent your hormones from pushing you along too fast. Examples would be "we are going to date for at least a year before moving in together" or "we are not going to see each other more than twice a week, to begin with".
We encourage you to choose wisely, given how hard it can be to put the brakes on a new relationship. If you are looking for a long-term relationship, patience and prudence shown now is a good investment for the long run.
• Verity & Nic are psychologists and family therapists who have specialised in relationship and sex therapy for more than 25 years. They have been working on their own relationship for more than 40 years and have two adult children.