Your Call: Should He Try to Win Her Back?

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We get a lot of advice questions coming in at, but sadly, we just can’t answer them all. Which is why, once a week, we turn to you to decide how best to advise a reader. Make your call by leaving your advice in the comments section below:

Dear Em & Lo,

I’m in a bit of a tricky situation.  I dated a girl for about 2 years, but then broke it off.  Long story short, the relationship soon stopped functioning at all.  We weren’t communicating with one another at all, we were both immature, and while we did care about one another, we couldn’t help each other through the emotional issues we were both having at the time.  So, while it was heartbreaking, I broke it off.

We spent the next year as, more-or-less, friends with benefits.  Now she’s with a new exclusive guy.  I’m really jealous, and I’m tempted to try and win her back, to try and get a better relationship working.  However, I’m incredibly adverse to mucking up a relationship (even though, by her own admission, it’s fairly casual, despite being exclusive), and furthermore, he has inoperable cancer, and she’s the only one who he seems to have let into his life in a really serious way.  So while I feel jealousy, I can’t help but feel for the guy, as he’s taken a big risk in dating at all.

Some friends have told me I should just try and find a casual date of my own, others have said I should try and win her back, and some have said I should do nothing and just focus on my teaching career and accept that dating just isn’t for me and try to absorb myself in work.  I’m horribly conflicted.  What do you think?

Completely Baffled

What should C.B. do?

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10 Comments on "Your Call: Should He Try to Win Her Back?"

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4 years 5 months ago

or do what Johnny said,, I just read his comment.. .

4 years 5 months ago

U should win her back…u only live once..if u truly love her..if not, do nothing and find another. No need to ruin the last months of the other guys life just to satisfy ur ego. Good luck..I wish my ex lover would try to win me back, but he dropped me like the hot pancakes he once made me in July 2007 and has never returned. I’m still heartborken over it.

4 years 6 months ago

Gotta say John, there’s a difference between being in love with someone and wanting a hottie who can cook. Everything you said you liked about her was really superficial, so maybe you’ll be less upset than you think if she does end up with someone else.

If I’m wrong, best of luck.

4 years 6 months ago

Talk to her. You never know how she feels. She might be willing to compromise with you. If she needs other people physically, try an open relationship or some type of less intense relationship for a while. If you really feel this strongly about her, don’t let circumstances scare you.

4 years 6 months ago

This is tricky. My best advice would be, if you are really determined that you want this girl, wait it out. If her current relationship ends, tell her how you feel. Then the ball will be in her court. You will either get what you want or at least get closure.

But, I have to say, I have been the girl in this situation. I have had a guy claiming to be “in love” with me after we had a very casual relationship. It really creeps me out that he thinks he is so attached to me when there is really no reason for it. You don’t want to appear in this light to this girl.

I think you need to take a step back and analyze what it is about this girl you can’t let go of. You probably would be better served doing as Johnny says and “chasing skirt.” Go get laid, have some casual fun, and see if you don’t find someone else. If you still can’t forget her, then maybe try to win her back.