Miss Information

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I'm sick of my virginity. Can I have a drunken one-night stand?

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Dear Miss Information,

I'm in a great relationship with a guy I really love and I know he loves me too. Everything is perfect except for one thing: he has a toxic ex. He and I have been together for seven months. About a year before we got together he had a really painful breakup from a four-year relationship. He had sort of grown up with this girl. It ended because she cheated.

In the first month of our relationship, we almost broke up because he wasn't sure if he was over her yet. Now he says he definitely is, but he clearly still feels a lot of anger towards her. He hates her with real fury and it kind of freaks me out. I don't really understand what her deal is at all. She moved to another country and cheated on him, but now she keeps trying to get in touch with him. We're very honest with each other, and he's told me that she tries to add him on Facebook every few months and has repeatedly messaged him saying she knows he's not over her. He replied first telling her to stop contacting him, but she won't stop.

Every time I even think about her I am consumed with jealousy and anxiety. I can't help but compare myself to her. We've discussed it, and I've admitted that I'm not entirely sure he's over her because he still hates her with such passion. I've told him that I can't feel secure in the relationship until I know that he doesn't care about her at all any more. He's said that he knows, and he's working on it, but it keeps coming back. It's like she's haunting us. He hates her so much he can't even say her name. Whenever he talks about how much he hates her, I can't help but think of that saying that there's a thin line between love and hate, and it really scares me.

Can I help him get rid of her completely? Can he hate her and love me at the same time? I love him completely and every other aspect of the relationship is amazing. I've never been so happy before and I can't see myself as happy with anyone else. He's the perfect boy except for this one thing.

— Hopelessly Devoted

Dear Hopelessly Devoted,

Though your boyfriend's ex may not physically be around, she is still able to wreak havoc and make you miserable. The more energy you both devote to hating her, the stronger she becomes — a she-who-shall-not-be-named who thrives on the unicorn blood of your fear and insecurity.

The feelings a failed relationship brings up — anger, betrayal, spite — are not necessarily conducive to carrying a torch, though. Your boyfriend is with you now, not his ex, and his unresolved feelings for her aren't evidence that he loves you less. You have already done the right things: talked about it, respected each others' positions. The best thing you can do is change how it affects you. Remove yourself from beneath her shadow. You are not her, and that is a good thing. Stop comparing yourself, and be the girlfriend you want to be.

Your boyfriend is obviously suffering, but his ex is his issue, not yours; only he can process it. Being supportive is great, but keep an eye on how much you can handle. You aren't responsible for helping him digest his past relationship, especially to the detriment of your own well-being. To regain your sanity, look at this as an exercise in getting power back: take the energy you had invested in fearing this girl, and invest it back into yourself and the relationship. Hopefully your boyfriend can heal enough to do the same.

Dear Miss Information,

Is planning to lose your v-card in a drunken one-night stand a good idea? Quick background: I grew up anxious with a kind of bad home life. I've been treated for anxiety and depression; I've been in therapy and plan to start back up again soon. Truth be told, I never gave myself permission to want sex until some point in my early twenties. I grew up in a culture that didn't make me feel like I had a right to be sexual unless I was married. I had one boyfriend, many years ago, and we only got as far as second base, because I was always aware of What Should Not Be Done. It kind of sucked for both of us.

In college, a gay male friend offered to sleep with me to just get it over with. I was, uh, touched, but decided against it. I broke my own hymen a few years ago because I was sick of having it around. I know virginity is a social construct, etc., but I feel really insecure about mine (and lately, really damn horny). A good friend has been in a dry spell of nearly two years, and when she found out about my problem, she asked if I wanted it to be special or just get it over with. Lately I've been leaning toward the latter, so she offered to take me out some weekend, find some guys at a bar, and see if we could both get some. I talked to her some more about how exactly that could go down, and I trust her and feel like we could keep an eye on each other if I do decide to go that route.

I think getting it over with would make me feel empowered, even if it was awkward. Another Old Virgin Friend (hey, indie band name) thinks I shouldn't do it like this the first time, but right now I feel like something is wrong with me half the time. I'm long past expecting an orgasm of rainbows and unicorns the first go-round. The question would be if I could loosen up, stop being so damn defensive, and get into the moment enough to enjoy it. (Alcohol would help, but with my meds, I'm not sure getting soused is the best idea.)

Also, do I owe it to the potential one-night stand to tell him I've never done this before? Part of me thinks I might as well, since he'd figure it out anyway. This is all assuming I could find a guy interested in me who I am also interested in — I have a really hard time seeing myself as attractive or worthy, as my last therapist pointed out. I'm working on it, but I don't know how to just fix that overnight, and I think I deserve to feel fuckable. I guess this really all comes back to that — I want to feel desired, even if just by a random person.

— Old Not-Maidenhead

Dear Old Not-Maidenhead,

Can I play melodica in your indie band? I've got some awesome patterns for cat costumes which we can give out free with our EPs. Call me! I've got so many ideas!

Band business aside: I understand where you're coming from, but a one-night stand might not be a great place to jump-start your sexual life. Regardless of how casual you want it to be, you're still sharing your body with another human, and that's a profound vulnerability for both of you. Good sex can be fantastic; bad sex can be alienating and depressing. Take ownership of the circumstances around the encounter, and it will be more fulfilling to you. This means stay sober, invest enough time to build some rapport and trust with the dude, and keep a finger on your emotional pulse. (And, when the time comes, it also means condoms, condoms, condoms.)

The fundamental principle here is self-respect. Sleeping with the first guy to buy you a PBR won't make you feel complete. (Hey, our first single!) You owe it to yourself to find a situation in which you feel empowered and comfortable — and sober. It doesn't have to be a Britney-Spears-in-Crossroads encounter, but it should be something you're fully present for.

In short, do it on your own terms, not in a rush or under any impairments. Go to a bar and make out with people furiously — which, I promise, will prove to you how "fuckable" you are — but be discerning when it comes to whom you decide to sleep with, and under what circumstances. It's up to you how long that process takes. Design the experience as something you can go into, and walk away from, feeling good.