Dating Someone when the “One that Got Away” Comes Back

Published on December 11, 2013

Many months ago, I worked with a reader on a struggle he was having with a woman he was talking to. As much as he worked to gain her interest, she never fully returned it. She would go on dates or communicate, then disappear. Or she would seem interested only apparently lose that interest in him a week later. Eventually she stopped responding and while hurt, he did get over her.

I talked about this type of situation in my last article on dating someone who repeatedly loses interest. However, this reader did move on, found a great woman to date and now, months later, the “one that got away” is contacting him again.

I’ll let his email describe the details:

It’s been long time I communicated to you. I had a date with a woman who I had zero expectations for. Things went smoothly and she started liking me and it was a successful first date. We are still seeing each other, although I am going out of town for next two weeks and she will be lonely. Right now she fears that I may not see her once I am back, although I can assure her I won’t do that.

The reason I am emailing you is because the woman I talked to you about before, she sent me an email asking if I can go out with her. It’s almost 7-8 months and it took me a while to get over her, but I am unable to understand that once she didn’t want to talk to me, what made her feel to see me again? I am not sure if I should trust her, and I also do not wish to make the woman I am dating right now feel insecure. I understand this is very weird question, but I would still like to ask, if you were in my position how would you respond to her (I mean the first woman) ?? she has now asked me to take some golfing lessons with her. Once again I really appreciate all your insights in helping people.

Recognizing Your Motivation to Communicate

You may find yourself in a similar situation: you were dating someone who never really showed interest. You moved on, found a solid relationship, but now the “one that got away” is contacting you again. I suspect most of us would really want to contact them. But why?

I think for many of us, we want to be valued by others. When we’re trying to date someone and they reject us, even if that rejection is through a lack of interest, we’re hurt. We feel like we’re not good enough and, for many of us, this type of situation can be rather depressing.

Then the person comes back and suddenly shows interest. Not only is the original attraction probably still there, but there’s also this attraction to be able to tell ourselves that we were “good enough”. Many times, it’s more than just whether you date the person or not: it’s also about how you feel about yourself.

So, odds are you’ll be very tempted to communicate with them if you’re in this situation. If you’re single, it’s fine (although I would again point you to my last article as the painful pattern could repeat itself). However, what if you’re dating someone now?

The Risk is Greater than You Think

First, let’s be honest: most of us will want to talk to the one that got away if they return, even if dating someone else. Most of us will tell ourselves something like, “It will be innocent and won’t go anywhere. I’ll just talk with him/her for a bit. And I can find out why they didn’t want to date and then I’ll move on. It will be easy.

I think this line of thinking is risky. Whoever you’re dating right now isn’t going to appreciate it if they find out. So you’ll want to hide it. Then if you end up having more than one conversation with that person, you’ll need to hide that as well. And you’ll probably convince yourself it’s still innocent. But these things get out of hand quickly.

My advice: don’t even give yourself a chance to mess up. I’d recommend you politely decline or not respond at all. Sure, the first few interactions will be innocent, but why give the opportunity for mistakes to be made? Especially if you like the person you’re currently dating?

Here’s part of how I responded to my reader:

If you really value what you have with this new girl, I would avoid communicating with the old one. I’m not saying ignore her, but I think it would be best to politely pass on meeting with her. I know you think nothing would happen, but why even put yourself in a situation where you might find yourself compromising on your values (again, assuming you really do like the new girl).

I understand wanting to know why she stopped communicating but honestly, to what end? I know it’s hard advice to take but you shouldn’t feel like you need to value yourself based on what this one woman thinks or what she did months ago. And if you’re not valuing yourself on her opinion AND if you’ve met a great new girl, I don’t really see any reason to take a risk.

An Exception
Finally, I’ll add one exception. If you’d prefer to date the “one that got away”, I think that’s fine. But:

1. Be honest with yourself. If you’re planning to talk to him/her so you can eventually date, admit it. Don’t play some game where you pretend you’re still interested in the person you’re currently dating or sneak around telling yourself it’s not going anywhere.
2. Understand that you’re taking a risk. You might find yourself in the same situation a month from now if they lose interest all over again. And now what do you do? If you go back to the person you were previously dating, now you’re just as bad as your “one that got away”! So be careful.

What are your thoughts? Have you ever had this situation and, if so, how do you recommend handling it?

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Author: Brad

Brad initially struggled with online dating but over time became quite successful using it. He met his wife using online dating and has been giving advice and helping people improve their results since 2007. He has written a Free Online Dating Guide to help others find success with online dating. You can learn more about his personal experience using online dating and running this website here.

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