Dear Miss Information, 

I've been going out with my girlfriend for about two years now, and we've done it countless times. When we first met, I was a virgin, and she had three guys under her belt. I told her I'd done stuff with other girls, but she doesn't know that it was little more than making out. Now, every time she tells me something about her past experiences, I have to lie and make up something comparable. But something's still bothering me: she tells me that she never got off with any of them — she didn't get wet or enjoy the experience in any way. I think she's lying to protect what little pride I have left. Wouldn't she have stopped her first three experiences if they really were "so awkward that it didn't even feel good"? I'm confused and angry, but I also want to get over it.  — Confused Liar 

Dear Confused Liar, 

Everyone you meet is going to come with a past. We date people, not Disney characters, and virginity doesn't indicate an absence of sexuality. I know virgins who have done more, seen more, and experienced more than those who've had intercourse. She's been with some people. You've been with some people. She could just as easily be jealous of these other girls. Yes, you didn't fuck them, but I'm sure she wouldn't like the idea of you kissing them, getting hard over them, touching their boobs, and so on. Sexual energy is sexual energy, so let's quit keeping score and call it equal.

Storytelling is good when it helps a couple get to know each other better: "What do you like? That's hot, here's what I like... Have you ever had anyone dominate you?" Storytelling is bad when it becomes a background check, a psychoanalysis, and/or a competition: "You did what? Eww. Your ex had a ten-inch cock? That's nice. My ex was a Yale grad and a stripper." Some people are too jealous to go there at all. Others set up rules: "no naming names," or "talk about the act, not the person."

It's totally possible that she slept with those three guys and didn't enjoy it. Sex is awkward in the beginning. You don't just come out the gate and do a triple axel. You fall on your ass a bunch of times and cringe twenty years later thinking about that cheesy costume you wore with the parrot headdress and the sequins.It's also hard to speak up in bed, especially when you're sexually inexperienced. Hell, even when you are sexually experienced. It's not like asking for extra ketchup at the drive-through.

So there you have it. Unequivocal proof of the possibility that your girlfriend was living a life of misery and sexual unfulfillment before she met you and your magical penis. Do you feel better now, knowing that she was uncomfortable and unhappy? Wouldn't someone who was at peace with their sexual past or at the very least neutral about it make a better, kinkier, and more open partner than someone who feels ashamed and conflicted? You need to ask yourself why you're so interested in getting every last stupid detail of your girlfriend's sex life before she met you, and even more important, why it matters so much to you that those experiences were negative.

Get your dick out of the past and focus on the present. Quit exchanging stories because clearly it's making you crazy. Is the sex good now? Is the relationship happy and faithful? If so, great. If not, get at what's really not working.

Dear Miss Information,

Would it be unequivocally, totally wrong to get with my good friend's brother? He lives near me; she doesn't (thousands of miles away, to be exact). He and I have become friends and it's clear there's attraction on both sides. Would it be okay to take it further, or does that violate some unwritten code? — Bro Love

Dear Bro Love, 

"Don't fuck my daughter," and "Don't fuck my sister," are cultural norms. They're the starting point for everything from sitcom plots to greeting cards to country songs. That said, while it's perfectly normal to look out for your family members, there's a fine line between saying, "Listen, I don't think you two would make a good match," and being Jessica-Simpson's-dad-at-a-purity-ball gross.

Your friend will probably think it's weird, just like I did when my sister started dating my male best friend in college. My sister kept me informed to the point of telling me too much. It got harder to talk to him once I had a realistic mental sketch of his genitals. I had to ask her to back off, and we adopted a modified version of "Don't ask, Don't tell." Conversations and dates are acceptable subject matter. The two Fs — Fighting and Fucking — are not.   

Could you and your friend work out a similar agreement? Be warned: it's way more difficult than it sounds. Because what do you do when you get in a fight with a guy? Call a good friend. Now you can't call that good friend, because the person making you mad is her brother. But you really want to call because she knows him better than anyone. You have to have discipline, though, because putting her in the middle like that is not cool. 

Talk to her before it goes any further. Feel her out. Ask her for permission to date him, even if you've already decided in your mind that you're going to go ahead regardless. Some people just want the formality of being asked, even if the answer if going to be yes. Are you and your friend's brother similar in age and dating experience? You'll get a much quicker blessing from his sis if the power dynamic is equal. 

There's always a chance she'll go crazy and tell you no way. Then you've got to make a call: friend or brother. I can't help you with that, though I would advise you to look at the big picture. Has she been a good friend to you, or is this one in a series of dramatic ultimatums? Is this guy just another cute face, or is he worth risking a falling-out?

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