I am a 28-year-old guy and I have a 24-year-old girlfriend. We're just three months into the relationship and it's going well enough that both of us are seeing some long term potential. What's been bothering me is a situation involving an "ex" of hers. This ex is a married man 30 years older than her, with whom she had an affair several years ago. I find that in and of itself to be a bit icky and ethically questionable, but the real problem is that she still keeps in touch with him and has fooled around with him several other times since the affair ended and she started seeing other people.

Not only does he still keep in touch with her, but he pines for her and makes attempts to get her back, including shit-talking me even though I have never met the guy. He has a secret Facebook persona so he can keep tabs on her and communicate behind his wife's back. I am uncomfortable with the fact that a man older than my own father is still trying to get into my girlfriend's pants. And I am uncomfortable with the fact that she keeps in contact with him, enabling his behaviour. Her rationale is that he was an important person in her life when she was going through some tough times. From my perspective, he was a horny old guy looking some action from a teenage girl.

I am also disturbed by the hypocrisy. She is fine with this guy cheating on his wife over the course of a half-decade, but otherwise wants to be in a monogamous relationship herself. I want to be in a monogamous relationship too, and I find her ex's behaviour to be deplorable. He's clearly not going to leave his wife, and she had no problem being his piece on the side. Her sense of loyalty to him over past "there for her" moments have left her unable to cut him out of her life; meanwhile, I am finding myself increasingly unable to just "not be bothered by it" as I become more serious and committed to this girl. I feel like I'm getting to the ultimatum point. And my question is, Dan, am I justified insisting that she cut off communication with him in order to keep me? If not now, when? And, can I argue my case that it is the right thing to do without playing the role of the jealous, pushy boyfriend?

Losing Sleep Over This

My response after the jump...

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Hm.

If this relationship—the one between your girlfriend and the creepy old dude (COD)—had long since transitioned to something else, something completely platonic, and COD wasn't pining or scheming, then you could be faulted for being "bothered by it." But COD is a mess (a fake Facebook profile? trashing his ex's current boyfriend?) and your girlfriend is either a mess herself (so messy she can't see COD for the POS he is) or a bitch (she's enjoying his misery, your misery, and, if she sees this letter, her appearance in the SLLOTD).

Take a deep breath, LSOT. You've only known this girl for three months. It's fine to be infatuated, it's fine to be picturing a future together already, but you don't really know someone twelve weeks in. You're beginning to get a sense of her character and her priorities and... well, there are some potential red flags here. Her relationship with COD could be a sign of major fuckedupedness. Or not. There are a lot of young women out there who think staying in contact with their exes—even messy, manipulative, cheating, lying, fake-Facebooking exes—is the "nice" thing to do. Lots of women have stayed in contact with toxic exes until they were forced to choose between pleasing/appeasing/placating an ex and pleasing/appeasing/placating a current. It would be better, of course, if a desire to please another man wasn't what it took for some women to cut off their toxic exes but... whatever works, works.

So my advice: give it a little time, get to know her a little better, and if you get the sense that she's a little messy but her heart is in the right place, LSOT, issue an ultimatum. She can have you in her life, someone with long-term potential, or she can stay in touch with COD, but she can't have you and COD. Tell her she's got to pick.

As for her hypocrisy where monogamy is concerned...

Good people have been bending their professed values over sofas and brutally violating them for as long as good people have owned sofas. Longer. We are each of us a mass of contradictions, LSOT. Maybe your girlfriend made an exception for COD because he's trapped in a loveless marriage—or managed to convince her that he is—and she felt sorry for him. Or maybe COD was hot, she was inexperienced, and she decided to go for it. Or maybe it was being in a relationship with a married man that made her realize just how much she valued monogamy. It's something you'll need to talk over with her.