My husband and I own a house, and we've been renting the extra bedrooms to help with the mortgage payments. But after several years of doing this, we've gotten to the point where we're ready to have our place to ourselves and lose the roommates. We asked our most recent renter to start looking for a new place in the spring and gave him more than four months to find a new place. Everything was good, and he seemed to understand when we explained our desire to have our own place again. But he moved out a week ago, and since then he has dropped by our house EVERY. SINGLE. DAY. One day, he texted, and we responded that we weren't home. Apparently, he came over anyway and just hung out on the back porch while we were out!

Asking him to move out and telling him it's because I want more personal space is apparently not clear enough. How else can I get through to this dude?

About to Dig a Moat Around My Castle

Looks like y'all got too chummy with your old tenant, and now he can't let go of the life he had with you two. This guy obviously thinks of himself as your very good friend now, and maybe he is, but he's spent so much time in your home that he obviously feels welcome to that space now, even when you're not there.

Next time you're all hanging out, take that time to tell him that you and your husband are ready to have your home to yourselves. See if you can turn your friendship into a public one—meet him for dinner, drinks or music, but refuse any offers of hanging out at home. Eventually, it'll become clear to him that y'all are bar friends and not friends friends, and that's gonna hurt him at first. He seems well-meaning, and I don't think there's a way you can do this without coming across as at least a little bit rude.

I've been sleeping with a guy for a while who is really obsessed with anal sex. He's pretty typical in that he's watched lots of porn in his life and seen it there, but he's never had anal sex before and has said that he wants to do it with me. We're pretty casual, but we're not in a committed relationship. I'm not into anal sex at all, but he's really persistent about it. I really don't mind if he wants to lick me there when he goes down on me or introduce a finger there during doggy-style sex. The only problem is that I can't help but think that he thinks he's going to ease me into eventually having anal sex with him. I've told him point blank that his penis will never enter my butthole, and I worry that my willingness to have anal play makes him think otherwise.

Exit Only

One of my exes had a preoccupation with the back door, as well, and he tried his best to nudge me into the act despite my insistence that I wasn't interested. I actually decided to break up with him on Valentine's Day (my first ever V-Day while not single, which sucks) after he got really drunk and literally tried to force himself into my butt mid-coitus. Things were going fine until I felt something knock-knock-knockin' on heaven's door. I actually looked up and said to him, “That's never going to happen.”

Your dude doesn't respect your boundaries, and he thinks he can push that boundary because you'll allow him to touch you there but not enter. You say you “don't mind” a little anal play, which sounds to me like it doesn't turn you on that much. I can really see that it gives you anxiety that he might try what my ex pulled. The bedroom is the last place you need to be having anxiety issues, so maybe you wanna take all anal contact off of the table. Taking that kind of play out of the bedroom altogether will show him how serious you are about that area being “exit only,” as you say.

I think you need to stand your ground with this guy in general. He sounds kind of pushy in a way that should not be happening in bed.

Need advice? Email [email protected], or use our anonymous form.