I couldn't figure out where to submit my question to you so I hope this is ok. Here's my problem.

My boyfriend and I have been together for a year and a half and I'm very happy. We are a straight couple. We have plans to move in together in the next few months. However, there's one very dark shadow that has been weighing very heavy on our relationship from the get go, and I'm at my wits end. He has an ex girlfriend from many years ago that he still hangs out with. They are very close and spend a lot of time together, and he tries to hide their meetings from me. He buys her nice gifts and takes her on outings. Every time I bring up how uncomfortable this makes me, he assures me that they are "just friends" and it's nothing to be concerned about. However, I know that she wants him back. Every time her name comes up or I find out they've been hanging out, I feel like dying.

I don't want to run his life, but he seems totally unaffected by how uncomfortable their relationship makes me. I feel like he is not ready to fully commit to me, since he is unwilling to let her go, and this makes me wonder if moving in together is a good idea. Am I being crazy? What do I need to do to become more accepting of their friendship, so that we can move past this? At this point, I feel like breaking up is my only option.

Third Wheel In My Own Relationship

My response after the jump...


Full disclosure: it's happy hour here in NYC and I've been getting happy.

Okay, TWIMOR, you open with "I'm very happy" but the very next paragraph closes with "I feel like dying." So I have to say... from the outside looking in... it doesn't appear as if this relationship is really making you too terribly happy. And as a general rule I generally err on the side of advising people to end relationships that make them want to die. Generally speaking.

And while I tend to take a dim view of current BFs or GFs or SOPATGSFs* who insist that their BFs or GFs or SOPATGSFs have nothing to do with their ex BFs, GFs, or SOPATGFs (see the letter below), the amount of time and money your BF is spending on and with his ex-GF seems excessive. It's one thing to remain on friendly terms with an ex, to get together now and then, to see each other socially and sporadically. It's another thing—or clump of things—to plan outings with your ex, to lie to your current partner about how much time you're spending time with your ex, and to spend money on "nice gifts" for your ex. Best case scenario: "troublesome emotionally affair/entanglement." Worst case: they're already fucking each other.

Still... if she wanted to be with him... and he wanted to be with her... why is he with you instead? Worst case scenario: because he's the kind of guy who can't bring himself to end a relationship so he's making himself intolerable in the hopes you'll end the relationship and then he can be with his ex again. Best case scenario: he doesn't want to be with his ex because he loves you and wants to be with you but he lacks the judgment to construct a relationship with ex—one with appropriate boundaries—and his stupidity and low emotional IQ is needlessly panicking you, his current GF, and he may wind up dumped, which is not what he wants.

Luckily, TWIMOR, there's a middle ground between "running his life," e.g. forbidding him to see his ex at all, and your BF spending as much time with his ex as he is now. Figure out what you're comfortable with—lunch or dinner once every other month or so, a small gift now and then to acknowledge her birthday or bat mitzvah or whatever. If he's unwilling to agree to that, TWIMOR, his "true" feelings about his ex are irrelevant. The real issue is his unwillingness to take your feelings into account and that shortcoming rises to the level of DTFMA.

I have a problem. A year and a half ago I met someone on DudesNude.com and we ended up meeting in May of 2013 during a layover in Toronto. I slept over and we had sex. We stayed in contact after I went back home but we decided to be friends only. Six months ago I met a boy and we connected really well and now he's been my boyfriend. He recently found out that I had an encounter with my Toronto friend and thinks it's inappropriate to remain friends with someone you've slept with. So now I have to choose: continue in my relationship with my BF and cut of my Toronto friend or vice-versa.

Please Help Me

It's common for gay dudes to become friends with casual hookups—hell, lots of gay dudes are best friends with one-time, one-off hookups. It works like this: since gay dudes, unlike straight dudes, draw friends and lovers from the same pool (other gay dudes), we sometimes we don't realize until after hooking up that the attraction was friendly, not sexual. We use our asses like sorting hats—this guy is Gryffindor (nice friend!), this guy is Slytherin (hot boyfriend!). Or something. Anyway. By ordering you not to be friends with that guy you hooked up with six months ago, PHM, your boyfriend has revealed himself to be not very bright, not very experienced, and not very insightful—and controlling and insecure to boot. DTMFA.

* "SomeOtherPointAlongTheGenderSpectrumFriends"