The Drew Barrymore Dating Game: A Hollywood Star Looks for Love on the Stern Show

Four lucky bachelors took a chance at romance with one of Hollywood’s biggest, brightest, and most beloved stars on Monday morning, joining the Stern Show to be contestants on The Drew Barrymore Dating Game. Hand-selected by Howard, his wife Beth, and executive producer Gary Dell’Abate, the quartet of suitors included a successful singer-songwriter, a Broadway actor, a martial arts teacher and comedian, and Stern Show staffer Jonathan Blitt.

“We feel Drew is a catch, so we set the bar high,” Howard said of the four bachelors.

Pre-Game Introductions

The rules of the game were simple: Drew couldn’t see the men, but she could ask them questions to find a match. Before bringing the acclaimed 47-year-old actress and talk-show host onto the show, however, Howard and Robin Quivers introduced the contestants to their listeners.

Bachelor #1 was 48-year-old singer, songwriter, and animal lover Joshua Radin, who once performed at Ellen DeGeneres and Portia de Rossi’s wedding. “You gotta meet somebody and settle down a bit, right?” Howard asked him.

“It would be nice,” Radin said. “I feel like I’ve always been ready, but I’ve never met the right person.”

Bachelor #1 was the first person Beth thought of when coming up with a match for Drew, but her connection to Bachelor #2 proved even deeper. “This is Clarke Thorell. He’s a very accomplished actor, singer, and musician on Broadway. He’s done it all — including date my wife,” Howard said with a laugh.

As Beth explained it, she met Clarke while he was performing in “Tommy” on Broadway. A few years later, they went on a couple dates. “We smooched a few times,” Beth said with a giggle.

“Why has a great guy like you never been married?” Howard asked.

“I’ve been in some amazing, beautiful relationships, and I still have love in my heart for every one of them … but I was seeing parts of my mom in all of them,” Clarke said of the women he’d dated.

“Bachelor #3 is no slouch either,” Howard continued, turning his attention to mixed martial arts fighter and stand-up comedian Diego Lopez.

“That’s an interesting combination,” Robin noted. “Usually, comedians become funny because they can’t fight.”

Diego assured Howard and Robin he was ready for love: “Long term would be great, especially with somebody like Drew.”

When Howard introduced Bachelor #4, staffer Jonathan Blitt, it was with a little less luster. “I can’t see how you can beat these guys,” Howard joked.

“I don’t see it either,” Blitt laughed.

Let the Game Begin

Drew Barrymore entered the studio ready to look for a match, but first the 47-year-old “50 First Dates” and “Never Been Kissed” star thanked Howard, Robin, and Beth for working so hard to find her a match. “I’m so grateful at the core of what this is – Howard and Beth thinking that someone, me, deserves to find someone,” Drew said. “Why are we not all out there doing this for each other?”

The entertainer didn’t want her suitors to focus on winning and losing, she just wanted them to be uninhibited and honest. “But if something clicks we’ll know what to do,” Drew added.

After the four men said hello, Drew was ready with her first question. “What was your process to decide to do this?” she asked the men, adding, “I said yes because I thought it would be fun, and I’ve been shitting my pants.”

Bachelor #3 thought meeting on a game show would make for a funny story with their eventual kids while Bachelor #4 – Blitt – had just jumped at the opportunity to meet Drew.

Drew’s next few questions dealt with children (the contestants don’t have any and they’re okay keeping it that way) and what they were looking for out of this experience. “I’m looking for something or someone who is open to exploration and taking it very slow,” Drew said. “I am a slow burn.”

Bachelor #1 said he valued trustworthy and kindness in a partner … before segueing into his relationship with his therapist mother. Bachelor #2 wanted someone with whom he could collaborate. Bachelor #3 wanted someone authentic, sincere, and kind. Bachelor #4 simply wasn’t looking for drama.

It was Howard’s turn to ask a question, and he had a doozy: “You’re sitting at dinner [with Drew and actress Cameron Diaz], and Cameron Diaz puts her hand in your lap. What do you do?”

Bachelor #1 would ask Drew if it were a test, Bachelor #2 shared an anecdote about his mom and started talking about threesomes, Bachelor #3 said he’d push Diaz’s arm off him, and Bachelor #4 said he’d yell at Diaz and leave the restaurant with Drew.

Drew questioned if the men had been genuine. “I think you’d fucking freak out and try to figure out how to get both of us in bed,” she laughed.

The Musical Round

Late-night star Jimmy Fallon made a cameo appearance, asking the contestants to perform an impromptu song about where they’d take Barrymore on their first date. Bachelor #4, a.k.a. Blitt, picked up his guitar and sang about St. Barts.

“Wow, you really did a song,” Drew marveled.

“This is so unfair … I don’t have an instrument. I don’t know where St. Barts is,” Bachelor #3 laughed before clap-singing his way through a song about taking Drew to a diner.

Bachelor #2 found a nearby ukulele for his song while Bachelor #1, the professional singer-songwriter, didn’t even try to top Blitt’s performance.

Next, Drew wanted to know what the suitors thought about “ghosting,” or disappearing on someone you’ve been dating with little or no warning.

“I think if women get ghosted [they’re] probably better off, and you should walk away and forget about that person,” Bachelor #4 said.

Bachelor #1 admitted he’d ghosted two people in the past … before feeling totally awful about it and sending them an explanatory message.

Talking about religion, Bachelor #2 claimed to be deeply spiritual, and Bachelor #3 said he was a straight-up atheist. “I consider myself an optimistic nihilist. I believe the universe is indifferent, and nothing happens for a reason, but that’s all the more reason we should be nicer to each other,” Bachelor #3 said, adding. “By all means have fun as long as you aren’t a dickhead to other people.”

Lightning Round

The contestants then answered quick questions about Brad Pitt, colostomy bags, how far they’d go to save their parents lives, how they’d respond if Chris Rock insulted Drew at the Oscars, and the last thing they did to make a woman laugh. For Bachelor #1, the answer to the question about making a woman laugh was dancing without his pants on. For Bachelor #2, it was singing in a Donald Duck voice. For Blitt, it was telling an Uber driver to drive an unsuspecting woman to Newark.

Drew complimented the men on their answers, making a special point of thanking Bachelor #2 promising to hold her hand and check in with her if she were ever insulted at the Academy Awards. “When he said, ‘I would take her hand,’ I almost burst into tears. I’m not kidding. Do you know how fucking long it’s been since someone has taken my hand and I felt safe with them?” Drew said. “That is the metaphor for life … Thank you, Bachelor #2. May all women and men out there protect each other more.”

Before selecting a winner, Drew asked the men a couple more questions about relationship histories, what they sought in a partner, and what they’d do if she didn’t select them. A couple contestants said they’d reach back out to her via social media, but not Bachelor #3, who didn’t want to clutter up her D.M.s. “I’d just continue with my day. I have a Zoom commercial audition later today that I’m really excited about not getting,” he joked.

Winner Winner No Guaranteed Dinner

With no further ado, it was time to pick a winner. “I’m firmly convinced you will fall in love and have one of the greatest experiences in your life,” Howard told Drew. “But now it’s up to you.”

Drew struggled whittling it down, so Howard revealed more information about each contestant to help her along. Finally, she came to a decision. “I will pick number two,” Drew said, selecting Broadway actor Clarke Thorell.

Drew would soon get to meet Clarke, but first it was time to get some face time with Diego, Jonathan, and Joshua — the three guys she didn’t pick. All three were good sports and Joshua, who said he’d never done anything like this before, suggested he’d probably still reach out to Drew in the future.

“I’ve never done anything like this either,” Drew responded. “I’ll invite you all to my next gynecologist appointment. I think I’ll feel less vulnerable.”

After that, Drew finally got to meet her match.

“Hi Clarke, how are you? I’m very, very happy to meet you,” she said before telling Howard she thought he was the safest choice because he’d copped to having chemistry with another woman. “We’re walking into this with very open eyes,” she said, adding, “I trust honesty. I’ve been deceived in my past and it’s not something I’m willing to go through again.”

Though she’d made up her mind, Drew wanted the world to know she planned to take things very slow. “Any outlet that says, ‘Oh, she picked Number Two,’ you’re missing the whole point of this story,” she said, later telling Clarke, “You and I are going to sideline and say hello and meet each other. We are not dating.”

Clarke could barely believe his luck. “It’s very surreal,” he said. “I’m just honored that somebody as beautiful inside and out as Beth and you, Howard, would’ve included me in this.”

“Honey, I could see why you fell for this guy,” Howard laughed.

Whether Clarke and Drew would fall in love remained to be seen, but either way the actress and talk-show host was thankful Howard and Beth had cared enough to set her up. “I will never forget this moment for the rest of my life,” Barrymore said. “No one has ever done anything like this for me. Let this be the awakening moment for all of us that we should all be doing this for each other.”