13 Dec 10

Sasha Speaks: Answering Your Most Private Dating Questions –- I’m Falling in Love With My Friends Step-Dad?

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Dear Sasha,
One of my very close friends has a new step-dad who is so amazing and cute. I’m in a spot since I think that he and I have developed strong feelings for each other. (I may even be falling in love!) He has just married my friend’s mom because he got her pregnant. He is also 10 years younger than she is (she is 37 and he is 27). I’m actually closer to his age, I’m 20 and my friend’s mom was a young mother when she had my friend at 17 years old.

Do I act on my feelings or not?

Falling in love with my friend’s step dad…

Paging Dr. Daddy Issues!

Listen up, Lolita, you need to back away from the penis and do it quickly and quietly.

What the hell is wrong with you? Are you seriously asking if you should be a home wrecker, destroying your friend’s family, breaking up a new marriage and turning an unborn child into an abandoned bastard?

You’re kidding, right?

You and I have never met but I’m going to go ahead and guess that daddy either loved you too much or not enough and now you’re on a constant quest for an older man to take care of you the way your real father didn’t.

Well, guess who’s your daddy now–me! And here are my words of sage advice…


It doesn’t matter how close in age you two are or how deep you perceive any feelings to be; that’s someone else’s husband and baby daddy, which means they called dibs and you need to show some respect. Meanwhile, if your friend ever found out about sick thoughts running through your head, I guarantee she’d never speak to you again.

When I was in high school, a friend of mine wanted to ask my dad to the prom. It wasn’t because my father is super hot, in fact he looks kind of like a love child between Woody Allen and Tom Selleck, but he’s a really cool guy. Her dad, by comparison, was a mean drunk who preferred Wild Turkey to his wife and kids. She asked if I would mind and I told her it was kind of weird so she decided not to extend the invite, but, from then on, I always thought twice about inviting her over after school and our friendship eventually fizzled.

If you don’t want to lose a good friend and ruin a new marriage just because you’re attempting to re-enact Poison Ivy, my advice would be to take a cold shower and give yourself a good hard slap.

*Feel free to email us with any dating, relationship, love and sex questions you may have for Sasha.

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About Jennifer Kelton

Jennifer KeltonI did not wake up one morning and say “hey I think I’d like a man use my sweater like a towel, write a candid dating book, become a dating expert, the CEO and founder of a social dating site and have three blogs.”

All of this has happened in a slow burn and here I am. The good, the bad, the mistakes, way too many tears shed to count, lots of wine and oh my goodness a huge learning curve that leaves me much of the time saying, “I’m sorry but this is all new to me.”

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