Dear Uncle Mat

Dear Uncle Mat,

My life’s a mess, but what’s new? That is why people write you, not because they are perfect. I am an educated, employed, handsome, nice guy. I live with two roommates who are also well-put-together gay guys in their 20s. All of us are single and looking for relationships, but with no real luck — except “Tom,” who has been dating the same guy for about three months now.

The thing is, I think I am in love with Tom: I was a little jealous of his new mate, then realized I have feelings for him. But wait, it gets better. About two months ago, I slept with my other roommate. We were buzzed, home on a Friday night, joking about how lucky Tom was, getting laid at his mate’s house. Next thing you know, we’re making time. We decided to keep it our little secret, and have been doing it more or less weekly since.

I just found out through a mutual friend that he told Tom a few weeks ago. It seems he thinks he is falling in love with me, but doesn’t know how to tell me. I think Tom is jealous, because I noticed his behavior has changed toward me for about this same amount of time. I am so confused about what to do. I like my other roommate just fine, but I don’t feel for him what I do for Tom. Tom also seems happy with his boyfriend (though I still think he is jealous about me). I am so embarrassed that this has all happened. It seems so trashy and tragic. It’s a total mess, and I am clueless how to fix it.

Please help,

Another Stupid Guy

Dear Stupid,

I would totally watch this on TV if I had cable. I’m just saying. I also totally understand why you feel embarrassed: Your situation is ridiculous, and it’s pretty much your fault. I don’t know that you are stupid, though. You are simply way more in touch with your penis than your heart. Happens to guys all the time.

Let’s take a moment and look at the positive side of this situation. You’re in love, or some approximation thereof. It is great to know and love another person. You’ve been getting laid regularly by another decent guy who genuinely cares for you. You have a home and a job. OK, so I threw in that last part, since the first two are only really good when taken out of context, but it does help a little, no?

Time to start cleaning up. First, you need to be honest with the non-Tom roommate. No need to declare your love for Tom to him, but you had best stop the sex and let him know that you are not interested in a relationship with him. Be kind and understanding. He may react poorly. Don’t react in turn. Remember, he may not be the only one in the house with an unrequited love. And who knows what else you are confused about. Do unto others …

After detonating that little bomb, let the dust settle before making any other sudden moves. See how the group dynamic reshapes, and work to maintain your friendships as best as possible. With both roommates. This shake-up may reveal more about Tom’s feelings for you. Again, take it easy. Jumping from one housemate’s bed to the next may seem insensitive and insincere, if not trampy — love or no love.

In a best-case scenario, where everyone remains at least friends, this conundrum should, at very least, serve as a lesson in boundaries with roommates: Be honest, and think twice before you put your penis in it.

I’m going to wrap up with a few observations you can take to your therapist’s office if you like, or just stay up at night pondering. You felt a little jealous about Tom’s boyfriend, so you slept with his roommate. Yes, I know he is your roommate, too, but you could have picked someone a little less … personal, no? What’s wrong with the roommate you’ve been shagging? You like living with him. You like screwing him. He loves you. Funny how the unavailable roommate is the one you want, huh?

Much love and luck,

Your Uncle Mat


Uncle Mat answers questions about relationships, sex, pets and art. Email him at [email protected],, or check out the Dear Uncle Mat Page on Facebook. Your true identity is safe with him.

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