4/29/11
Your Call: Should He Try to Win Her Back?

photo via Flickr

We get a lot of advice questions coming in at EMandLO.com, 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?

Best,
Completely Baffled

What should C.B. do?