When You Can’t Let Go of an Ex

May 5, 2011


I worked so hard for that first kiss

And a heart don’t forget something like that

Tim McGraw



A note from Robinson:

Hi Susan,

My ex girlfriend broke up with me 6 months ago (we dated 3 months) and unfortunately I am still emotionally suffering from the break up. We are very different people, although we did have a mutual interest in wildlife biology. She enjoys getting wasted, smoking weed and hooking up (she likes the attention). I have avoided drugs throughout most of my life and have never hooked up. Our differing values were not compatible and are what led to the break up.

As a male, I’m embarrassed (sarcasm) to say that at the mighty age of 24, I lost my virginity to this girl. I was brought up on the values to seek meaningful relationships and I do believe I achieved that in this case. The problem is that I can’t seem to get past this girl who I don’t even want to be with anymore. Since I lost my virginity to her and put a lot of effort in the relationship, I still can’t seem to shake the feeling of a sort of innate obligation to take care of her, be there for her and love her. Why do I still feel that way when I really want nothing to do with her? Could there be a biological explanation? Or do you think its more likely to be environmental?

My relationships in the past did not involve sex and I never felt that strongly about them. I hate to say it, but after being emotionally drained by this relationship, I have the urge to fall for the temptation of hooking up with no strings attached. I know its not the road I should go and I know I will not do it, but why do I all of a sudden have this urge when I have resisted it for so long?

I’m curious to know if this happens to other guys who lose their virginity in a relationship. They have a relationship, lose their virginity, relationship ends, the cost of being in a relationship is too high and emotionally draining, they resort to hooking up. What do you think?


Hi Robinson,

I’m sorry you’re feeling stuck and sort of obsessed about a relationship that ended. I know that’s a terrible state to be in, and maddening when you know that you don’t even want to be with her. You don’t say who ended the relationship, but I’m going to assume that she was less invested overall than you were.

It sounds like she was your first real love, and you sealed the deal with sex in a way that was extremely meaningful and important to you. Having had prior relationships and held off until you were 24, it’s not surprising that she would hold a special place in your heart. Even after a bad breakup, when we don’t like the person anymore and may even disrespect them, it’s common to long for the old relationship, back when it was new and wonderful and seemed pretty close to perfect.

You’re troubled by continuing feelings of obligations and even love towards her, even as she clearly repels you in some ways. There are several reasons why you might be having these feelings, including any combination of the following:

1. You liked who you were when you were together.

I’m sure that the two of you as a couple raised some eyebrows – a case of total opposites attracting. The idealistic and uncorrupted male with the drunken party girl is an unusual pairing, and I imagine that was novel and exciting for both of you. Plus you were really into her, which made you feel great and fun and generous and sexy.

2. You loved that feeling of being head over heels, so that even as your value differences became more obvious, you held on.

The relationship, while troubled, was still so much more than you’d ever experienced with another woman. Perhaps you were afraid you wouldn’t find this kind of intensity again. Or you were hopeful that she might change.

3. You projected an idealized version of who she was, and that’s who you really fell for.

That’s who you miss today, and part of you still wishes it could work out. From your letter, it sounds like you recognize her need for attention and validation from men, and you openly admit she is a lush and a pothead. It sounds like you romanticized her when you first met.

You may have even thought she needed rescuing. If you went into the relationship with the idea of taking care of her, supporting her and loving her, you must have been frustrated when she didn’t allow you to do that fully. That could only have worked if she did indeed share your values, and wanted to live them, with some help from you. Instead, it sounds like she very much maintained her independence and her old ways.

4. You realize she fell for an idealized version of you as well.

You may have found it difficult to keep her interest or sustain the attraction over time, as the differences between you became more evident. You had not only different values, but also the very different histories that went along with that.

The dynamic would have given her the power in the relationship, which she no doubt enjoyed. She had the sexual experience, and probably some cynicism from the no-strings sex, or at least the ability to compartmentalize her feelings. In a prior era, you would have had the power by deciding whether you could accept her past indiscretions, but today she is the one living the “cool” lifestyle. You held fast to your own principles, which is commendable, but again, your way is not the easy way, and it’s not the way most young people live.

5. You feel humiliated by the rejection.

The end of a relationship is a failure, there’s no getting around it, and it’s always painful, even if it’s what you want or know is best. It’s easy to internalize that and feel like the one responsible. It takes two no matter how bad things get, so you do have some responsibility. My guess is that if you have any sense that you were not “bad boy” enough for her, you will look inward and blame yourself further, even though it’s clear that you are the one more oriented towards relationships.


Whether you can relate to any of these possibilities, or have other theories of your own, understanding them won’t make you stop longing to take care of her and love her right away, but gaining some insight into your own emotional triggers can make you more rational and ready to move on.

Now to the second part of your question – Do guys who lose their virginity in a relationship and become disillusioned when it ends then want to start having no-strings hookups?

I hope that some of the regular commenters here will chime in and offer some thoughts on this question. I haven’t received this question before, but I can’t imagine that it’s unusual to feel that way, particularly if you had to let go of some long-held beliefs about women and sex.

On the other hand, perhaps the experience was so costly and emotionally draining because you were not with the right woman.

You may have specific regrets about how you handled things, or you may just need some time before you are ready for another commitment. Whether you should pursue short-term casual sex at this point depends on how congruent that is with your nature and your needs. Frankly, I don’t see how becoming more like her makes sense when it was her values that drove a wedge between you.

There is a saying in Game: when you get really stuck on one woman and she disappoints you, you should go FTOW (f*ck 10 other women) to get her out of your system. I’d hate to see you go that route, but if you do I urge you to be up front and open with your partners.

Robinson, what are you looking for? What would make you happy? Be honest with yourself about that, and then figure out the most effective strategy. That process begins with thinking about how you will choose differently next time around.



Readers, help me out here. What are your thoughts for Robinson?