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My ex has been waiting for me for two years – do I go back to him or let him go?

Ask Roe: I feel if I don’t give him another chance I’ll always wonder ‘what if’, but I don’t want to waste more time

Dear Roe,

I’m a woman and I am 33. I got with my ex-boyfriend when I was 27 and we broke up just before Covid. He wanted to get married but there were issues in our relationship; we would fight a lot over issues that never seemed to get solved, like his immaturity and irresponsibility around things like jobs and money, and communication issues that upset both of us. He is funny, kind and was very loving and affectionate, but I felt like I was always nagging him, and if we got married I’d always have to be the responsible one. All the fighting got exhausting so I broke up with him. But this was close to the start of Covid and we never really stopped talking. I moved back in with my parents in a different county so we didn’t see each other in person, but we really got each other through the pandemic. This year we’ve met up a lot and he’s told me several times that he wants to get back together and that he doesn’t want to date anyone. I’ve been on a few dates but they have been either awkward or horrible, which makes me feel I’m making a mistake not to hold on to a man who is so romantic and crazy about me. I’m torn because we still care about each other and aren’t fighting, but I don’t know if it’s a good idea to get back together. I do want to get married and have children, and feel if I don’t give him another chance I’ll always wonder “what if”, but if we do get back together and it doesn’t work out I will have wasted more time. How do I decide what to do?

When thinking about getting back together with an ex, there are usually many layers of emotions and reasoning going on, and I can’t pretend that I can make this decision for you. But my instinct here is that going back to him isn’t the right move for you, simply because all these reasons you allude to aren’t reasons that are pushing you towards your ex, but reasons that are helping you hide from other emotions and possibilities. You are quite articulate about your fears both about the relationship (the unresolved conflicts and communication issues, his irresponsibility, your fears about a long-term relationship dynamic), and about remaining single (the difficulties of dating, not finding someone as affectionate, losing out on time to have children). But all of these are avoidance-based reasons. I don’t feel any advance-based reasons; reasons that are actively and positively pushing you towards this relationship.

I may be wrong, but I think what might be helpful for you is to start asking yourself – and possibly your ex – some questions, and really being honest with yourselves about the answers.


The first thing you need to ask yourself honestly is why exactly you are still so close with your ex? Of course some exes can be friends, but you and your ex never had any emotional space from each other and as he is still professing his love for you, it’s clear that your dynamic never transitioned into the realm of the platonic. He is obviously hoping to get back together, but what were/are your reasons for breaking up with him but never letting him go? Is it because you were hoping that the shock of the break up would make him want to change to win you back, so you could have everything you wanted? Or was holding on to your connection a way of bypassing some of the feelings associated with the break-up?

We often overlook the experiences of the person who ends the relationship. But breaking up with someone you were serious about and with whom who discussed marriage can hold a lot of different emotions: grief over both the end of the relationship and the unrealised hopes you had for the future; guilt for hurting them; and the fear that you are making a mistake. I wonder if remaining close with your ex was your way of trying to avoid or bypass any of those feelings.

Of course, in your case, there was also the sudden and traumatic onset of Covid, where we were all suddenly much more isolated, there were fewer distractions, fewer opportunities to date, and so remaining in touch with someone who knows and cares about you would have understandably been a hugely important source of support.

But now that the world has opened up again and your ex is still expressing his desire to be with you, I think it’s important to get clear on your reasons for staying in touch with him – for both of you. Feeling guilty for ending the relationship or being scared of regretting the break-up aren’t good enough reasons to go back to a relationship that will keep you stagnant. And, importantly, neither are they good enough reasons for stringing him along, which is – intentionally or not – what you are doing. You know he’s not dating anyone because he’s still invested in you, and because you’re letting him believe there is hope. Your ambivalence and desire to keep your options open is preventing him from getting over you and moving on with his life. That time you fear losing, whether to him or to dating other people? He is currently losing time to your indecision, which isn’t fair.

If you were serious about getting back together, you and your ex would need to have some very open, honest, and focused conversations. Do you both understand why you broke up, and have you individually worked on the issues contributing to the break-up – has he, for example, become more responsible and worked on himself to develop emotionally, and have you worked on your ability to set boundaries so that you no longer take on more than your fair share in a relationship? Do you now share a vision for a future relationship and relationship dynamic, and do you agree on how can you work together to make that a reality? Do you both understand how you have grown and changed in the years since you first met, and are you both ready and excited to meet each other as you are now to create something new, instead of holding on to outdated ideas of each other? How do you both want to grow as individuals in the future, and do you think this type of growth will be possible and encouraged within the relationship?

If you can answer these questions and feel excited to try a relationship again, then go forth and good luck. But if you don’t feel reassured and excited about the answers, or if you find yourself avoiding even asking the questions, then do what is right for both of you and end this dynamic, firmly and finally. You have been important figures in each other’s lives, and you can respect that while giving each other the space and clarity to move forward with your lives, and find relationships that don’t hold you back, but bring you into your future.