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My Boyfriend Refuses To Try Anal

We've talked about it, but he says no every time.

Q: I have been dating my boyfriend for two months. Everything is great except he won't do a certain thing in the bedroom that I actually like. Yes, I'm talking about anal. I like it and would like to do it with him. We have had discussions about it, but it's a flat no every time. Don't get me wrong—there is no issue when it comes to sex otherwise, but I still feel unsatisfied sometimes. I just want him to try it once for me. What should I do?

A: No matter who's on top or bottom, or whether you're in front or behind, you've got to respect each other's boundaries. No ifs, ands, or but(t)s. There's nothing wrong with asking for what you want. It's great that you're being honest. And it's good that your boyfriend is being honest too. But you'll need a unanimous vote to pass this backdoor diplomacy.

It's only been two months. As you're together longer, hopefully your trust builds and you expand your repertoire—and maybe you gradually pry open that backdoor. Foremost, I'd give him some time. There's also nothing wrong with a little friendly bargaining. Maybe you'll discover there's something he craves and you can concoct a trade: Scratch his back, and maybe he'll get behind yours.

The key here is to clearly express your desire without pressuring him. Think about how you would feel if your boyfriend wouldn't stop trying to persuade you to do something with him. If anal turns him off, you have to accept that. It's always fine to explain what you like, but it's never cool to keep pressuring someone after they've said no.

Q: I've been hooking up with one of my really good guy friends for the last couple months, and it's been the best thing ever. We've got the perfect balance between friendship and sex, and he's recently been initiating most of what happens between us. But I was recently at a party with him, and his ex showed up (side note: they were together for over three years and broke up nine months ago), although he was hoping she wasn't. Long story short, they made out and she gave him a blow job at the party when I wasn't around. I found out later that night that it's happened a couple times since he and I began hooking up. However, he told me that he felt horrible about it and like he was cheating on me while it was happening, even though we aren't technically together. We ended up spending the night together after she left and I woke up to him kissing me. I don't want a relationship with him, and I know what he and I have is strictly just messing around. Am I allowed to be pissed that he's been hooking up with his ex and he didn't tell me about it?

Yes, you're allowed to be pissed off. You're always allowed to feel anything—no feeling is wrong. And you can certainly share this feeling with him. But that doesn't mean he's done anything wrong or that you should have expected anything else.

When you don't set a limit, there are no limits. Period. You say, "I don't want a relationship with him," and it sounds like you've never had a specific arrangement.

Just because you're having sex with someone doesn't mean that they're obligated to tell you about anything else they're doing (and that's one reason safe sex is so important). You can't just expect monogamy—or anything else. You have to talk about it. But that doesn't mean having "the talk"—as in, a talk about a full-fledged relationship. Even when sex is casual, you can set certain limits. The trick is this: You actually have to ask for them first.

This guy made no promises. He didn't break any either.

Q: I just started seeing this guy, and we have gotten pretty close pretty fast. I'm getting really close to him, but I'm worried about his ex. He has her name tattooed on him and he isn't in a rush to get it covered up, and he still talks to her every day. What worries me is their history because they dated for four years. Should I let it go, or should I be worried?

Your boyfriend dated her for four years and still talks to her every day? Hell yes, you should be worried! You don't have to look for a warning sign: It's literally tattooed onto his body.

You don't have to break up with this guy, but you should be very skeptical. Maintain your boundaries, don't let yourself fall head-over-heels, and open up a conversation about his ex—so you can confront your worries head on. It's fine to be friends with your ex. It takes time to shake off your attachment after a long relationship. But this is a little extreme. Be careful.


This article originally appeared on Minor edits have been made by the editors.