Don’t Ask, Don’t Tell, Don’t Really Know

“I feel kind of guilty,” Serena told me. “He didn’t ask if I had a boyfriend, but I also don’t want to lead him on. I’m only in it for the sex, but does he really need to know that after our first night together?”

“Well, it was your first date,” I sympathized. “Who says you have to lay out all your cards right away?” 

Serena, who’s 39, lives in San Francisco while her boyfriend lives in New York. They’re madly in love, but recognize that sometimes you just need to take care of business—with someone else. That said, they’re both allowed to see other people, but only for sex—no love, romance or long walks on the beach. (I forgot to ask whether sex on the beach was OK.)

Serena’s boyfriend told her he’s had massages with very “happy endings,” while she’s met some nice guys including the one with whom she had “amazing mind-blowing sex” with he other night—you know, the one who still doesn’t know she has a boyfriend.

When do you release your stats—age, relationship status, fetishes, sexual proclivities—to the person you’re dating?

My friend Mira is 49 but looks 32 and is one of those tall, blond stunners who leaves guys with their jaws sitting on the floor in her wake. Just last weekend, she went out on a date with a new guy. “He’s 47. I know he thinks I’m 35, and I’ve decided I’m just not going to tell him that I’m not.”

Herein lies the conundrum. If you refuse to share your age, for example, and it’s obvious you’re not 24, what happens if you do tell? Are you really hurting someone by withholding said information?

Patricia is a beautiful woman who regularly struts through my neighborhood. I’m guessing she’s in her late 50s, not that she’d ever tell me. “It’s not that I have a problem with it,” she said. “I know I look great. It’s that other people have a problem with it. Society says if I’m a certain age, I have to act and look a certain way. I don’t need the added stigma as a woman.”

However, Jen, 27, who lives in Boston, told me she likes to get everything out in the open so that she doesn’t waste any time. With no hang-ups or secrets to hold her back, the sex is better. “Why not have the best sex you can have?” she told me. “Why have even one night of bad sex?”

So I asked Jen: Don’t you worry about the possible stigma that personal stats could bring were you to share them with a guy? Are you worried a guy will think you’re a slut if, for example, you share your sexual likes or fetishes with him? (This is a concern many woman share, which keeps them from, well, sharing.)

“No way,” she said. “Just the other night I told this guy whom I met at your party that I need to be spanked to reach orgasm. Damn, he had great rhythm.”

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