A Drunk Screenwriter, Actor Wannabes and a Petty Thief: Hollywood's True Tales of Online Dating Nightmares

Dating Nightmares Illo - H 2015
Illustration by: Zohar Lazar

Dating Nightmares Illo - H 2015

One in three "I dos" now originate digitally as the industry gets hot and heavy into Tinder, Grindr and OKCupid, and everyone's motive (and potential embarrassment) is under scrutiny in a one-industry town: "I'm not sure if he was looking for love or work or both."

This story first appeared in the July 24 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.

Dating in L.A. has always had a bad rap. "Particular to Hollywood are successful entertainment businessmen in their 30s and 40s going home with anyone they want — and women getting paid to be pretty," says Talia Goldstein, professional matchmaker and founder of (the ironically named) Three Day Rule. "This makes this town more superficial and particularly brutal for the rest of us." But with the advent of Tinder (and, as of July 7, Tinder Verified), plus a slew of increasingly niche online dating sites and apps, Hollywood hotness — once the exclusive domain of the glamorati — at last has become democratized, with multitudes of executives, production assistants, celebrities, screenwriters, interns, tech moguls and, yes, even billionaires swiping, clicking and searching online for their next husband/girlfriend/one-night stand/future ex, all mostly within a 23-mile radius.

In this one-industry town, digital dating (which as a national industry brought in $2.1 billion in 2014) has created annals of awkwardness unique to Hollywood. It includes daters spying industry colleagues behind Photoshopped pictures and managers trying to meet people outside the business but consecutively failing many times over or having one's dates insist on sharing their acting reels. At least the discomfort can pay off: In 2014, one in three marriages originated from a computer or mobile screen. And while digital anything always has been attractive to millennials, the fastest growing demo to get wired for connectivity is the over-50 (Viagra'd) crowd. Mark Brooks of Silicon Valley's leading branding firm for online dating companies, Courtland Brooks, sweepingly attributes a number of occurrences, both good and bad, to the explosion of smartphone dating apps, aka the "Tinderization" of modern courtship: lower prostitution rates, an increase in interracial marriages, more pickiness among singles, a higher divorce rate, more cheating and more one-off dates (i.e., booty calls). How very rare in Hollywood.

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The 3-year-old app Tinder, with 85 percent of users under 35 and 40 million downloads, has swiftly become part of the daily lexicon. "Swipe right" and "swipe left" now are synonymous with yes and no, hot or not. But for a Hollywood club that con­nects you with the geographically convenient and desirable, it isn't exactly VIP-private. After breaking up with John Mayer, Katy Perry tweeted that she's "deep on Tinder," while Andy Cohen, Eric Stonestreet, Hilary Duff and a still-married Lily Allen all are admitted swipers. Even Brian Grazer's ex-wife Gigi Levangie Grazer says she met her current boyfriend on Tinder. With its purely looks-based premise, the app does have cringe-worthy moments: When Lindsay Lohan scrolled through one night in search of hipster guys … she found her brother. One well-known female TV comedy writer recently took a first-time Tinder date to her favorite comedy club: "Halfway through the act," she says, "the comic mentions Tinder, and my date leaps up and yells, 'I'm on a Tinder date!' I saw people I work with snickering and was mortified."

Brooks explains the app's popularity: "What's made it catch fire is that it's fun, and online dating can feel like work. It's brought new heat to the industry and is benefiting everyone," including Tinder president and co-founder Sean Rad, who met his girlfriend Alexa Dell (daughter of tech billionaire Michael Dell) on his own app. "What we've done," says Rad, "is take rejection out of dating." And now with Tinder Verification, which celebrities can apply for, notables can prove they're the real deal and not catfish.

Rad has expanded the app ("We don't pigeonhole Tinder as a 'dating app' ") to include branding, with pop star Jason Derulo launching his "Want to Want Me" video exclusively on Tinder via a faux profile to 39 million views and Mindy Kaling and Chris Messina putting up profiles as Mindy Project characters (right-swipers were rewarded with a sneak preview of a new episode). Says Rad, "Suddenly, all the big studios are hounding us with promotional ideas." Madonna promoted her Rebel Heart album to a captive audience on Grindr, another location-based mating app but aimed at gay and bisexual men, and a collaboration between the app and Nicki Minaj is on the horizon.

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While these apps (plus a new one called Hinge, which uses Facebook friends as a meeting pool) are heavily used by a younger demo, grown-up Hollywood professionals are coming out of their digital-dating closet via sites such as MillionaireMatch.com, dedicated to one-percenters seeking other one-percenters. All participants are vetted for income, which probably is why Matthew Perry prefers it. With 2 billion page views a month, Match.com has the most and broadest dating options (Melissa Rivers, Jenny McCarthy and Martha Stewart have indulged). Plenty of Fish, another broad spectrum site, gets action by remaining free (both Patti Stanger and Sinead O'Connor are fans). But the artsier and quirkier OKCupid, which has grown to 12 million users, attracts the most cultured Hollywood component at the moment, even as "the cool place-to-be rotates all the time," notes a female producer in her 40s. To reclaim some cool, Plenty of Fish, or POF, is collaborating with Kesha, Lady Gaga, Flo Rida and Britney Spears to get namechecked in their videos. Not to be outdone, Match found a way to be the featured dating app in Mariah Carey's "Infinity" video, in which she shows off her own post-divorce profile.

Also trending are niche sites with lower numbers but more like-mindedness, targeting food preferences (GlutenFreeSingles.com, VeggieDate.com); intellect (AlikeWise.com for book lovers, Geek2Geek.com); looks (BeautifulPeople.com); age (OurTime.com, SeniorPeopleMeet.com); and, yes, gold-digging (SugarDaddie.com, with 1 million users). "I even tried FarmersOnly.com to find a kinder, gentler guy," says a top female manager. "Then Cupidtino.com, the Apple fanboy site, to find Silicon Valley geeks. In the end, I went back to OKCupid. I met a nice Jewish agent who lives two blocks from me."

The industry stampede toward dating apps is not without its hazards. Former Fox vp and founder of PR firm Hive Bumble Ward, green from a long marriage that recently ended, had a newish date, a screenwriter, come to her house for a casual dinner party with friends: "I think he was nervous. He drank a bottle of tequila and passed out on my couch. And didn't wake up till the next day, humiliated," making it unlikely he'll be getting work from that crowd. "Next, I met a man who claimed to be a director, and I represent directors. When he found out, he said, 'Babe! Maybe you can get me a job. I'm a card-carrying member of the DGA!' I'm not sure if he was looking for love or work or both." She didn't give him either.

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With celebrities dipping a toe in these uncharted waters, it can get even choppier. "I swiped on an actor on Tinder," laughs a veteran PR woman. "He didn't swipe me, but later he came in for representation. Needless to say, I didn't sign him." One L.A. marketing exec with her own firm met on Match a well-known actor with whom she indulged in a fling. "Months later, I was working a Golden Globes suite, gifting celebs, when he strolled in. I ran and hid. I was so mortified. I didn't want to seem like a celebrity kiss-ass." A female TV personality was thrilled to date a famous baseball player on Plenty of Fish, which transformed them into a power couple favored by the media. "Then a year later, when we mutually broke up, every outlet in the world covered it, reporting he dumped me."

Add online dating's temptation to misrepresent to the new fluidity of sexuality, and the lines can blur even more. One gay stand-up comic met a fawning young soundman at a gig "who asked me out for drinks and flirted for hours. Then he told me he was bisexual. Then he said he was married. Then he said he'd never been with a guy before. Then he told me he had three kids." A female agent swiped a cute guy on Tinder who appeared to be "seeking women" but at the end of a great date pronounced he was gay. "I thought I wanted to try women out," he said. "But actually, I don't."

With everyone becoming expert Photoshoppers from Instagram, a picture's worth much less than a thousand words. One female director went to meet what seemed like an attractive playwright … who turned out to be 300 pounds: "He'd only posted a head shot and his face looked thin." Men aren't the only fibbers: An independent film distributor met a blind date at a bar in Brentwood but didn't know she was there for a half-hour: "She'd doctored her pictures so much, she was unrecognizable. After she left, I discovered my wallet gone and I had a $200 bill." A well-known author in her 60s bravely flew to Florida to meet a retired TV producer her age — only to discover he's in his 90s.

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The rise in teen sexting has given some adults the wrong idea. One female writer met "an elegant opera snob/classical musician." They agreed to attend the symphony. Then he sent her a full-body naked photo, which was "anything but elegant. Particularly for a man of 50." Online dating has seen the rise of the "virtual affair," a florid epistolary romance that ends the minute meeting becomes a reality. "I told this writer on Match that we needed to meet for coffee before any long email exchange," explains a female art director. "After he sent two five-page-long emails, I deleted him. You could spend months corresponding with someone you don't meet, only to have them turn out to be an ogre or a specter."

Brooks admits digital dating could improve: "We've taught people a new way to meet people. Now we have to teach them how to keep people. People need to reveal themselves more. The future is in combining digital dating with wearable tech, which will allow the sharing of certain personal data: what music you download, where you eat, where you travel." Video also will add authenticity, says dating coach Eric Resnick: "With mobile phone screens getting larger, that's a natural. And now that gay marriage is legal, we'll start to see gay sites geared toward serious relationships." Jokes Ward, who suggests more openness will lead to longer romances: "What we need now is a dating app called Tender!"