Miss Information: The girl I like has the worst boyfriend ever — I want to tell her, but how can I be sure I’m not being selfish?

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The girl I like has the worst boyfriend ever — I want to tell her, but how can I be sure I'm not being selfish?

Photo by Cindy Ho

Have a question? Email Letters may be edited for length, content, and clarity.

Dear Miss Information,

I'm eighteen, and my boyfriend and I started dating in the couple months before the end of our senior year in high school. That summer, we exchanged "I love you"s, decided we were "ready" to have sex, made a big deal of picking out condoms together, and waited for the perfect opportunity. We didn't have to wait very long, because a week later my sister told us we could have the guest room after a house party at her boyfriend's house. My boyfriend didn't want us to be drunk for our first time, so we slept it off and decided we'd try in the morning. We were hungover and I wasn't really feeling it, but I was nervous and excited to make him happy, so we went ahead and tried — but he couldn't get hard. We laughed it off; I didn't think it was a problem, and he told me it was because he was hungover.

Since then, we've tried to have sex six times. He's stuck in a self-fulfilling prophecy and I can't do anything to help coax him out of it. Whenever I've suggested trying to have sex, he's always gung-ho, but when the condom goes on he goes flaccid. It doesn't take much to get him hard when we're fooling around, but he gets really nervous when it comes to sex because of our history of failed attempts. I love him and we're in a serious relationship, so this isn't a dealbreaker (and we're both virgins, so I guess we don't know what we're missing) but we're sexually frustrated and I don't want him to feel inadequate about not being able to do something we both want. Is there any common-sense solution to this?

Frustrated Virgin

Dear Frustrated Virgin,

Sex doesn’t begin and end at penetration. Let up the tension by telling him you love him and you don’t care if penetration happens tonight or not. Say it and mean it; all sex is "real sex," and penetration shouldn't be on a pedestal. Then fool around and see what happens. Invest in some sex toys to help the effort. If you can find mutually satisfying alternatives, it may calm his nerves. Sometimes condoms themselves can be the problem, but make sure you have an alternate birth-control method before you even think about going that route. (Do I need to refer you to the many teary arguments on MTV’s 16 and Pregnant? Don’t test me.)

There also may be something else going on. Maybe he’s terrified of getting you pregnant, maybe he’s petrified he’ll “do it wrong,” maybe the ghosts of an Evangelical upbringing are whispering in his ear. If you think this might be the case, ask him if something is bothering him, then give him the space to answer. If he has an answer, great. And if he doesn’t, trust him and drop the subject.

You’re right to be sensitive to his nervousness. Good sex is built — it doesn’t just “happen.” It will take both of you as a team. So let go of your expectations and thoughts of “what are we missing?”, and do what feels good. You’ll get there.

Dear Miss Information,

I have feelings for one of my close friends, but have accepted that nothing is going to happen because she's in a committed relationship. The problem is, her boyfriend is awful. He's constantly insulting her, canceling plans she's been looking forward to for weeks, disregarding her goals in favor of his own, and aggressively flirting with other girls in front of her. If she were any other friend, I'd be advising her to dump him immediately and find someone better. In this case, however, when she asks for my advice, I tell her to give the guy a break, because I feel if I tell her to end it I'm doing it so I'll have a chance with her. Is there a way I can tell her to get away from this creep without seeming selfish?

— Wants What's Best For Her

Dear Wants What's Best,

The question about your motivations could go either way, but here's the tipping point: the phrase “when she asks my advice.” If she’s asking you to weigh in, it’s because she has some misgivings. And if she has misgivings, that means there are already cracks in the relationship. That’s the good news! The bad news is that you’re not exactly on the H.O.V. Lane of the Friendship High Road by lying to her. If she’s asking you point-blank about her boyfriend’s behavior, she wants a point-blank response. You’re doing nobody any favors by demurring or lying. What gets accomplished? She settles for a douchebag, he happily crushes beer cans on his head, and you’re left in the corner to pen your Heartbreak Album opus.

So pick the option that feels most honest to you — which, judging from your tone, is telling her what you see. You’re certainly entitled to express concern over how a friend is treated. But also know your limits: you can tell her once, but don’t beat her over the head with it. Ultimately, staying with him or breaking up with him is her call. You can throw in your two cents’, but then back off and let her make her decisions, whether or not you agree with them. If she ends up wanting to be with you, it won’t be because you broke up her last relationship; it will be because you proved yourself to be a worthwhile guy.

Dear Miss Information,

I just recently got back in touch with a guy I dated for a few months, a year ago. The sex, as it was before, is completely amazing. We also have a lot of fun together. Last time around, I fell for him really hard and he couldn't commit, so I stopped seeing him. He got in touch with me this time around. Does that mean he's ready to be serious? How do I make sure I don't go out on a limb with my feelings again? I've been trying to protect myself; he tried to kiss me in public the other day and I gave him the cheek. He got angry. But kissing in public is something I do with boyfriends! How do I protect myself without limiting the potential of this relationship?

—  (Girl)friend? With Benefits?

Dear (Girl)friend?,

Until you tell him what you want, you can’t expect him to magically divine it. Most likely he got back in touch because he likes you and because he liked what you had. And you clearly like him, but you did not like what you had. Eek, an impasse! So you’ll either have to meet somewhere in the middle, or one of you will have to bend, or one of you will get hurt.

The easiest way to stop the latter from happening — as well as the most emotionally honest response, in general — is to ask him. Maybe he did see the error of his ways, and is now totally on board The Commitment Train. Or perhaps he’s hoping that your natural chemistry with him will win you over and that you’ll meet him more where he is, i.e. enjoy something casual like before. Your hesitation is totally understandable, but sending mixed messages — “let’s hang out! Let’s have sex! But no no, don’t kiss me in public!” — doesn’t help. It will just confuse him, which will add to your confusion, and then nobody is on any trains, commitment or otherwise.

So ask him, but know that it doesn’t have to be a big, intimidating feelings/weddings/unicorns affair. Give it to him straight: “[Dude name], I think you’re the bee’s knees. But remember how we broke up last time ‘cause you wouldn’t be my steady? My feelings haven’t changed. Ya dig?” (Anachronisms optional. I find they add an extra “pizzazz” to tough talks.) No matter what happens, you’ll come out of it stronger: either the relationship will stick, or it won’t, but you’ll a) have the reassurance of knowing, and b) respect each other, and yourselves, more for giving credence to what you want.