Hollywood's Over-40 Female Dating Hell: Gavin Polone Searches for Solutions (Guest Column)

Illustration by Hanna Melin

Some guys have gone gay. Others like to be mistaken for their date's father. Now, one male producer surveys his female friends to figure out why industry players can't find love — and why his happiest singleton is "OMing" (yeah, you'll want to read that part).

This story first appeared in the 2015 Women in Entertainment issue of The Hollywood Reporter magazine.

I am not particularly attractive. Not being modest, just honest. At 51, I'm rigidly set in my ways — some might even say I'm "spectrum-y" — and I have a lot of opinions that don't correspond with those of most people. In short, I'm no bargain. Yet during periods when I have been single, many people offer to set me up with their attractive and successful female friends.

Conversely, I can never think of any men to fix up with my numerous friends who are attractive and successful women in their 40s and 50s. Obviously there are men out there — Los Angeles isn't a reverse China, where government policies have altered the gender ratios — but if I think of men I know who are between the ages of 40 and 60, who are single, who aren't trolls, who have a job and who aren't guilty of some extreme Hollywood transgression like being a Republican or a nanny-fucker, it isn't a huge number. And the best of those men are gay. What's left are a very few — and all of them seem to have a predilection for, and the ability to attract, much younger women.

I don't think any of my female friends anticipated that when they emerged from their failed marriages their pickins would turn out to be so slim and unsatisfying. If life were fair, the right man would be available to them now that they've worked out their issues, done most of their child-raising and have successful careers. And yet it seems so few are finding anyone good. Or maybe my perception is skewed by a relatively small sample size.

So I decided to step outside my usual circle and interview some successful, attractive women I know less well.

First I turned to Celia (all names have been changed), a producer in her mid-50s with four kids. "I would like to be in a real relationship, but I can't quite envision how it would work in my life," she said. "He has to be in my circle. I need to know that he somehow has an intellectual interest and likes discussing things — essentially, a smart Jew. I've tried all the dating sites. All JDate has is a bunch of Israeli contractors who live in Encino; that would be interesting and fun, but not someone who would fit in my life. Who would I bring to my kids' graduations? Nobody has anyone who matches me."

I asked Celia if she thought those men who do meet her criteria were being taken by younger women. She agreed. She also said she sees some "second-chapter gay men who had wives and families — they take away not one guy but two guys from the database. Also, guys who want an Asian second wife: You come home, they cook you dinner, you get a blow job, and that's it. They sort of serve the same function as the gay guy."

So where does that leave her? "I have a few booty calls on my list," she added. "I've done the young, athletic stud; I've done the Nigerian doctor. I haven't done a woman yet."

I asked Celia if she might look for her own second-chapter lesbian situation.

"It has been suggested to me as a potential route," she said. "But lesbians are very relationship-driven; you don't go to your own corner in a lesbian relationship. That is too much for me — I just don't want that much intimacy."

Next I spoke with Mary. She's also a successful producer, is in her late 40s, has one teenager and has been in and out of relationships during the 10 years since her separation. "I don't think I necessarily want to get married, but now, going into the next few decades, it would be great to have someone to be with," she said. "The guys I've gone out with are attractive — I can't go out with someone I'm not attracted to. Chemistry is a big factor. I get hit on by so many guys in their 30s but nobody in their 40s, and I won't date younger. And if a guy is in his 40s and not married, it's a flag."

Gulp. Is that strike two or three for me? I've lost count.

"And guys who come out of a 20-year marriage haven't had much sex in the last 15 years, and they're just into the availability of women," she added. "The odds work in their favor in a way they didn't when they were in their 20s. My ex-husband has a much bigger pool than I do: He can date a woman in her 20s or 30s who wants to have another child; I don't want to have a baby now. Also, I think the financial thing plays into it a lot: My ex can date a billionaire or a waitress. I need to be careful of two types of guys: 1) opportunists; and 2) a guy who is not interested in Hollywood but who will feel bad about himself from being around my lifestyle. I was with a guy for four years, and my success magnified his own failings in life. When I would have success, he'd say, 'Things come so easily for you.' "

Meeting people is hard, especially outside the business. So Mary goes online: "I like the idea that you know people in common, like on Hinge. Raya [a dating app that caters to the creative community] is pretty vetted — it is a good site. You have to give them access to your Facebook and Instagram, and they decide whether or not to let you on. But when I first went on that site, it was all guys in their 30s, and my age range [45 to 60] wasn't there. I've been on Tinder, where I'll only go out with someone if we have Facebook friends in common.

"When you're in your 20s, you are evaluating who can be a good father or provider. Now my list is, who am I going to connect with sexually and romantically?" she added. "I've always waited for situations to come to me, but today I said to somebody, 'I've never asked you this, but if you know anybody …' "

Finally, I contacted Dorothea. She's a television executive and has been dating for five years since her long-term marriage ended. She has two kids. "I got out of my marriage, and I felt so depleted," she said. "Many women are working so hard, and their husbands aren't giving them enough. Since I've been divorced, I've done a lot of work on myself. Women have been falsely conditioned and removed from their own power and pleasure. If they want to have a relationship, they need to become the kind of person who can attract the person they're looking for. Be the source of your own pleasure."

"But," I asked, "how does your acting differently change the math of finding a guy?"

"If you take out all of your preferences and what you've been trained to think you want, there are a million great guys out there."

"Which preferences?"

"Short men are a flavor; so are tall men. You can open up the possibilities of what can turn you on. Take age and education out of the equation. I dated someone who was 24 when I was 46. It was fun — he made me feel young."

"Didn't that large an age difference present problems?"

"If you really think you're going to have a serious relationship, you're not going to get what you want. There's an expiration date on that kind of relationship," she replied.

Of the three women, Dorothea appeared happiest and most optimistic. I asked her what type of work she'd done on herself, and she mentioned having participated in a program called OneTaste. I went on the website expecting it to be like all the other self-help, confidence-building offerings out there. But I was mistaken.

The centerpiece of OneTaste is something called orgasmic meditation, or OM, where a woman practices "OMing" with a "stroker" who rubs the woman's clitoris in a specific way, both giving her pleasure and helping her with a meditative experience. The stroker is not necessarily someone she knows, or even is attracted to, but rather another participant in the program or an instructor.

"The way we go about relationships feels like we want to pin them to a wall," explained Dorothea. "People want to quantify them. OMing is all about what feels good to you. That isn't selfish — it opens up the space. And then you're finding something attractive in everybody. This makes it so much easier to meet somebody; I've gotten to experience each man I have been with and each gift he had to offer me. They were not men I would have considered before, and I allowed them to make me happy — and then I made them happy."

Once I got over my initial prejudice against anything "new age-y," I definitely could see how being more matter-of-fact about orgasms would necessarily allow one to widen her dating pool. After all, it's a big step to take your pants off and let a semi-stranger, to whom you might not be attracted, help bring you to orgasm. If you can do that with your stroker, maybe you also can be happy with a guy who doesn't offer the qualities you thought you needed in a man.

Still, I can't get on board with the idea that great women should have to change their preferences to fit what is available. It's the men who are pursuing younger women who should be changing their preferences and see that it is creepy to be with a woman who reasonably could be mistaken for their daughter (except Sumner Redstone, 'cause that's just sweet). I don't want to be with someone that young, and I don't know why any woman that young would want to be with me — other than for financial reasons, which makes me want them less. There are a lot of great, successful middle-aged women available, and men their age should start taking advantage of that fact.

Polone is a film and television producer.