Dear V

Dear V: Man, she’s not feeling like a woman …


I‘m dating a girl that likes to wear a monocle, and it kind of creeps me out. She wears a monocle because she likes to think she’s an old-fashioned detective, and she likes to think she’s a 60-year-old man when she’s having sex with me. 

She wanted to try role-playing recently to spice up our relationship, and now I’m creeped out by how much she’s dedicated to her role. Either I’m sleeping with an extraordinary actress or a sociopath. What should I do, V?

I think I’m dating Albert Nobbs 



Dear Sally Field,


Your situation exists in one of two scenarios: Your girlfriend has either seen “Mrs. Doubtfire” too many times, or she’s psychologically damaged and needs to be helped.

I’m not one to judge a person’s personal preferences, and I don’t think I’m the ultimate judge of what gets someone off, but cross-dressing to the point where you turn into a grandfather in the bedroom sets off lots and lots of red flags. This chick has daddy issues that not even Freud himself could decipher.

It could be that she’s one of those artsy types that just likes to experiment with herself and the concept of fluid sexuality. If we take a step back and look at this in a larger sense, this experience could prove really beneficial for your sexual repertoire. This girl could be the one to expand your horizons, and no matter what any other woman throws at you in the future, you’d be able to handle it because when you were in college, you were hooking up with a girl who wanted to dress like a 60-year-old dude in the sack.

If I were you, I’d suggest some other role-playing options of your own, and if she’s receptive then knock yourself out.

But, we also have to remember that not every sexual encounter is going to be an extravaganza. You all are so concerned with “spicing up” your relationships, but how much spicing up do you need? We’re all in our 20s and have libidos like wild animals.

Tread carefully and make sure she’s not going to kill you in your sleep. But before then, have a conversation about what your sexual relationship is really about. If you only want to see this girl for kinky sexual encounters, then a conversation isn’t needed.

Maybe if you dress up like a 60-year-old lady, you’ll balance each other out. Just make sure your prosthetic nose doesn’t fall off.


March 23, 2014



Advice Columnist

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