I was asked out on a date by a lovely woman about 8 years younger than I am... and I really don't know if I should accept or not. The thing is how I met her. That's what makes me wonder if this is a good idea or not.

A week ago I hired an female escort for an half an hour of oral sex at her place. Three hours later we were still banging away in every position imaginable. Afterwards I apologized for taking up so much of her time and she said she got horny too and it was her choice. We spent the whole next day texting and sexting with each other and she asked me to go see Fifty Shades of Grey with her when it opens this weekend. I asked if she wanted me to join her as a client or as a date. She replied: "As a date." We spent one more day texting, and the day after that I went to see her again for some coffee and some more very fine sex. Not as a client, but for free as a friend or fuckbud or whatever we are now.

I like her, we hit it off, and the sex was mind blowing. (She enjoyed it too, at least as far as I can tell.) I wouldn't mind seeing a lot more of her. I don't really care that she works as an escort. I can't handle monogamy anyway so open relationships are what works for me. But still... I thought things like this only happened in cheesy romantic comedies with Richard Gere. Part of me things she's just being friendly to get a regular customer. But if that was all it was would she have had sex with me that second time? Or asked me out on a date?

Should go out on the date, spend time with her, and see what happens? Or should I be more careful and cynical and end it because she might just be playing me?

What would you do, Dan?

To Date Or Not To Date

My response after the jump...

I got in a little trouble answering the exact same question—"What would you do?"—in last week's Savage Love. A married woman in a dire situation (thirty years of lousy sex, the prospect of dying without ever once having great sex) wanted to know what I would do if I were her (cheat, cheat, cheat). The controversy made the leap from the comments thread on the column to two successive SLLOTD installments. Things didn't settle down until after BIBFAULT, the woman who has never once had really good sex, wrote in with an update and shared some additional details that 1. retroactively rendered my advice TOTALLY AWESOME and 2. got me out of the doghouse with my readers.

And now you come along, TDONTD, asking the exact same question: "What would you do?" If I had any sense I would duck the question—"It's not about what I would do, it's about what you should do"—but "having sense" isn't my style.

So what would I do? I would go out on the fucking date (even if it meant sitting through Fifty Shades of Grey), I would continue spending time with her, and I would stick around to see what happens. Great sex, a strong personal connection, more great sex—that shit doesn't come along every day, TDONTD, as BIBFAULT's experience demonstrates. IMHO only an idiot walks away from great sex, a strong connection, etc., for fear of being played. Yes, she could be playing you—but so could anyone. A doctor, a lawyer, a debutante, another escort: anyone could be playing you. But which do you think is the more likely scenario, TDONTD: This sex worker actually likes you and wants to keep fucking you because she's a human being who wants a romantic and sexual connection with a primary partner just the same as any other human being... or this sex worker looked up "How To Turn a Guy Into a Regular Client" in the Sex Work Handbook and found "fuck him for free" in there somewhere?

All of my friends who are sex workers have or have had significant others. It's rare for a sex worker to date a client—it's rare, TDONTD, but it's not unheard of.