Why Am I Jealous of My Boyfriend’s Ex?

Oh Evan, I need your insights both from a dating expert and male perspective! I am currently dating a loving man who calls me beautiful everyday, loves me deeply and has given me absolutely no reason to mistrust him. The problem is, we shared too much about our exes and none bother me except for one woman who broke up with him (in many other cases he broke things off first).

The problem is I think her overconfidence about her looks paired with her flashy work convinced him she is really something special. They only dated briefly before she dumped him, and my boyfriend says she was flaky, shallow, and never saw a future with her. I am intelligent, more attractive and I’m not worried that he’ll go back to her, but it really bothers me that he was attracted to someone so shallow to begin with. Even after they broke up he contacted her again when he found himself in between other relationships.

So Evan, I must ask, why would he try to go back? And here’s the biggest question of all: Does his continued interest in her make him shallow/lacking in values too or does this just make him a man? I’ve never dated the toxic men you describe so often, and always thought I’d date a similar man who would laugh at these kinds of women, not pursue them, even if it’s now in his past. In your experiences, how do men deal with attractive women who dump and bruise their egos? I’ve often read that you’ve dated many very attractive (but perhaps not shallow) women, so I’d love your expert opinion. My greatest fear is not that I am second best, but that I am perceived that way. Should I just get past this or get past him? —Smith

Oh, Smith,

Ready for Lasting Love?
Ready for Lasting Love?

Let’s say I had a client named Marie. Marie is 43 and recently got out of a 10-month relationship which had no passion whatsoever. Nice guy, but he didn’t make her laugh and she didn’t respect him.

The last time she was on Match.com, she was kind of creeped out, so she decides to lay low for awhile. Maybe travel a bit, take a breather from dating, reconnect with some old friends that she’d pulled away from in her last relationship. She goes on Facebook to start the process.

I would think that just about everyone reading this can say that they’ve gotten in touch with an ex shortly after a breakup.

Browsing through names of friends, she happens upon her ex-boyfriend, Jay. Ex-boyfriend might be too strong a term — but he’s the guy that she had incredible sex with for three months back in her mid-30’s. Jay wasn’t a great communicator or ready for a relationship at the time, but he was cute and fun and smart. Marie sees that he’s single on Facebook and pops him an email: “Hey, was just thinking about you and wanted to see how you’re doing. What’s up?”

Is there anything remotely unusual about this situation? Is there anything that’s particularly hard to understand? Marie is newly single, lonely, and is grasping for some drug to make her feel good. She concludes that it would be easier to go back to an old well than to try to tap a new one. Is this a smart long-term decision? Probably not. But I would think that just about everyone reading this can say that they’ve gotten in touch with an ex shortly after a breakup.

So, Smith, your “problem” is really much ado about nothing.

You’ve got a devoted, trustworthy guy who treats you well and happens to have a hot, selfish ex in his past. What a coincidence! I have one, too!


And before she unfriended me on Facebook (because no single woman wants to see a happy ex-boyfriend with his new wife and kid), I would even occasionally look at photos of her online. Why? Because she was hot and I wanted to see what she looked like in her 40s. It’s not much more complicated than that.

If my wife were to judge me for the short-sighted, tortured, ill-fated relationships in my 20’s, instead of say, judging me exclusively on how I TREATED her, we might never have made it. Thankfully, she didn’t. And as a result, she knows all of my past sexual history and isn’t remotely threatened by it. And because she isn’t remotely threatened by it, I never feel the need to lie to her about anything. And because I never feel the need to lie to her about anything, she feels closer to me and 100% safe in our relationship.

Was my ex-girlfriend from 2000 more physically attractive than my wife? Yep.

Is my wife second-best to a woman I dumped after 4 months nearly 12 years ago?

You have got to be kidding me.