Miss Information

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Dear Miss Information,
It’s my biggest fantasy to watch my girl bang another man. She gets hot when we talk about it, especially in the bedroom, but she keeps saying she’s too scared to try. How can I get her to cross over that imaginary (but very real) line? — Two Minus One


Two Minus One,
Dude, CALL JOHNNY DEPP. Seriously. Who would refuse a threesome with that man? He’s so universally hot even my grandma and my IKEA garbage can want to fuck him. Actually, that’s a lie. I don’t think Johnny Depp is that comely. The facial hair is a cross between Lovesexy-era Prince and a homosexual catfish. Yuck.
You say very little about why your girlfriend is scared. Have you asked her, or did you stop at no and move on? The next time the topic comes up, see if you can draw out a few more details. Preferably this won’t be done while you’re in the heat of the moment, in bed. It’ll sound like wheedling. Do it sometime when there’s less pressure. Possible reasons just off the top of my head are:
1) She’s afraid you’ll view her differently afterwards. Instead of a girl you watch Netflix with, she’s become some kind of crazy sexpot.
2) She’s worried she’ll fall for the other guy. Even worse, you’ll fall for the other guy.
3) She’s seeing it as a one-time thing, but you’re harassing her to do it all the time.
4) She tried to get into it, but it just felt awkward. She didn’t want to do it but was afraid of letting you down and went ahead anyway.
Talk to her about best-case/worst-case scenarios, and keep in mind that you can approach this in steps. You don’t have to go from zero to double penetration. You can have makeout parties, heavy-petting sessions, and so on. Hell, you guys might find you get everything you need and stop there. No need to go all the way.
Final word of advice: Let her take the lead picking the guy. Keep in mind that the world isn’t teeming with people willing to do this. It may take some time. Meanwhile, see if you can get her to amp up the dirty talk or start exploring another fantasy. There’s a chance this one will never happen.


Dear Miss Information,

I went on a date with a really great gentleman. We had dinner, which included a large bottle of wine. Since I’m not much of a drinker and I was pretty out of it, he suggested he drive me home and we spend the night at his house. Long story short, I ended up sleeping in his bed. Nothing happened, we just kissed. Since then, I’ve been distraught. I feel as if I’ve ruined the chances of a serious relationship, and made him see me as a floozy rather than the nice, mature woman I am. I’m newly divorced and not used to dating, but I want to get it right this time around. How can I have a serious relationship with someone I go home with the first night? — Regretting the Vino

Dear Regretting the Vino,
Was there some all-night sex session that I missed? Did I miss a few lines about watersports and hamster bondage? You went on a date, drank some booze, and made what the overwhelming majority of non-celebutante adults would consider to be a responsible decision not to drink and drive. Then you took the goody two-shoes act a few steps further by refraining from sexual intimacy before you’re ready, something that’s hard to do when you’re all liquored up.
I don’t think the relationship is ruined, but all this nervous, high-strung behavior could put it in jeopardy. You made a mistake. Alcohol will do that to you. And nerves. And first dates. And dating after you’ve been single a long time. Two New Year’s resolutions I want you to make, Vino. The first is regarding ass, the second is regarding alcohol:
1. ASS: I will go on dates with my eyes and ears open. I will make decisions in my best interests, and not take things so seriously all of the time. I will not offer myself up for anyone’s judgment, or assume that said judgment is correct or relevant, without taking all other factors into consideration.
2. ALCOHOL: I will not drink so much the next time. I will alternate alcoholic beverages with non-, and eat a big meal before or during the event. I will recognize booze-pushing behaviors when they occur (“Let’s do a shot!” he says, ordering before you can resist) and engage in clever deflection (“Awesome!” you say, “I’m going to give mine to that grizzled old Vietnam vet at the end of the bar.”)
There was a time for taking a guy’s word as law. That time was called high school. Developmentally, you’re still there, because you’ve been out of the dating game a while. But things are different now. You can go all the way without being a ho. It takes a lot to be called a ho these days. Trust me. If you’re not comfortable with a certain behavior, just take an analytical approach. “Hmm. I don’t feel good doing that. I’m not going to do that again.” Then that’s it. End of self-flagellation.
Dear Readers: Here’s a question I didn’t have space to get to in this week’s column:
At what point is it okay to give the single parent you’re dating advice or input regarding how to raise their child? The reader in this situation wasn’t talking about anything serious — the kid was throwing a tantrum in a grocery store and the father wasn’t (in the dater’s opinion) doing enough to shut him down. Three months? One year? Engagement? Marriage?
Leave your comments in the Feedback section. Work it out.


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