Some Dates Are a Shame

By Lainie Speiser

One of the sexiest images I conjure up for myself during my “private time” is the memory of a lover I had who put one or more of his big, meaty man fingers in his mouth, get them nice and wet and then use them to finger me. It just gets me going every time, the memory of seeing him doing this from my laying back vantage point, looking up at his big ole body getting ready for some serious play and doing this one little act. I don’t know why but it sends me shivers every time.

So, when I read about actor/comedian Aziz Ansari on about his much-reviled date with the young lady now known to the world as “Grace,” sticking his bony (in my imagination), long fingers and sticking two of them down this woman’s throat repeatedly before fingering her, I practically shrieked out loud, “WHAT? You’re doing it all wrong! UGH! You’re so stupid!” If only Aziz read my column, his career wouldn’t be the disaster it is today.

While I don’t think anyone who is asking a lady or gentleman out on a date to get laid is a crime, being in your mid-30s and not having the faintest idea on how to seduce a woman should be. Aziz did it all so wrong; it just goes to show you, being famous with lots of money somehow doesn’t help you buy a clue when it comes to female pleasure. I wish I could rewind that whole evening for him and coach him through it, and then he’d still be known as that lovable, funny, feminist with the charming show on Netflix (“Master of None”).

When I’ve had bad experiences like this with men who are old enough to know better, I’ve wondered why no woman stopped this guy in the past just to say, “Hey that’s not how you do it, allow me to show you the proper way.” As I got older and more confident, I tried to be that woman as a public service. I was once on a date with a handsome man in his forties who after a few minutes of making out thought it was perfectly okay to try to jam his thumb up my ass. Yes, you read right. We were making out on my couch, and I was straddling this strapping, sexy beast, his arms were around me pulling up my sundress— and bam! I felt a big ole thumb between my big white cheeks. I stopped him and said, “Whoa, whoa, whoa you haven’t even touched my tits yet, and you’re trying to put your thumb in my butt? C’mon now!” He looked at me strangely then started to laugh; his face was bright red, then he said, “Okay Miss Lainie, tell me what you want to do.”

I admit, I’ve read the play-by-play of Aziz Ansari’s epic date fail more than once, more than twice, but definitely less than five times. A New York Times writer who wrote a piece in defense of this sexually clueless man said the piece read almost like pornography, to which I thought, he wishes! But no, I didn’t get a thrill from reading about how Aziz points at his penis when he wants a blowjob, or that he calls pouring another glass of wine a second date (an old, hacky joke), or that he keeps trying the same thing, like sticking two fingers in a V sign down his date’s throat over and over to the same lukewarm results. No, I keep reading about it because I can’t believe there’s been such little progress in sex and dating since I was 22. Not only on his part but also on hers.

Life can be very uncomfortable, and sex can be downright awkward and embarrassing. What’s great about being an older woman is that you don’t feel this need to please everybody as much as you want to please yourself. But I don’t want women to have to wait another 10, 15 or 20 years to have the ability to recognize when a date isn’t working for them. It only perpetuates bad behavior from men; if you don’t open your mouth and express yourself while it’s happening, nothing is going to change for the better. Maybe Aziz thought everything he was doing was fine because nobody else ever expressed to him that he was doing it wrong. I’m giving him the benefit of the doubt because I don’t want to think he’s just a selfish prick. This is a guy who wrote a best-selling book about modern romance after all. Unfortunately, with a lot of men, their sheer lust and desire supersede noticing that their partner isn’t having a good time.

A gorgeous friend of mine, Sabrina, went on a date with a millionaire a bit ago. He wasn’t famous, just your garden-variety Silicon Valley success story. They met at a party that I brought her to, and I was excited when he asked her out. The date started well; he had a town car pick her up with a rose waiting for her on the seat, and took her to the trendy little bistro. The millionaire then ordered an appetizer for them, then proceeded to eat most of it himself, without a thought that she might be hungry. Then he took her to a trendy, exclusive club for dancing. When the car dropped them off at the club, and they were walking in, he stopped, grabbed her, and shoved his tongue down her throat for a sloppy, bad first kiss. “I know I’m attacking you, but I don’t care,” he said with a big ole dopey smile. I’m proud to say Sabrina didn’t care either— for him that is— and abruptly called it a night, no town car needed; she said she could get home on her own. Later he texted her and wrote, “You left your rose in the car, how sad.” I later found out from the millionaire’s personal assistant that this grab-and-tongue move was his go-to move. I’m sure if he’s still single, he probably still does this. Some people never learn, and some people who are in positions of power don’t feel they have to.

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