Chelsea Handler Talks Matchmaking, Dating Advice and Drew Barrymore's Past on DREW BARRYMORE SHOW
The comedian also sits down with Yamaneika Saunders and Jared Freid to debate dating dos and don'ts.
Chelsea Handler used a sit-down with Drew Barrymore to encourage fans to shoot their shot, telling Barrymore she is happy to serve as an unofficial matchmaker for people hoping to slide into her direct messages. The comedian's appearance on THE Drew Barrymore SHOW tied her dating commentary to her "High and Mighty" tour, giving the conversation a promotional anchor while Handler leaned into her reputation for blunt relationship advice.
The first clip finds Handler walking Barrymore through what it means to play matchmaker for her audience, describing the tour and the kind of direct, unfiltered encouragement she gives fans looking to make a move. The exchange sets up the looser, more personal territory covered in the two roundtable segments that follow, both filmed with guest host Valerie Bertinelli alongside comedians Yamaneika Saunders and Jared Freid.
In the second clip, that roundtable turns toward Barrymore's own dating history, with Handler cracking that "everyone has made out with David Spade" as the group digs into the actress's past relationships. The moment plays for laughs but keeps the focus on Barrymore herself, with Saunders and Freid adding their own takes as the conversation moves around the table.
Additional footage from the same roundtable shifts to dating advice, with Handler and Saunders sparring over the idea that a woman should "let the man choose you." The suggestion draws pushback in the room, with Freid and Bertinelli weighing in, turning the segment into a broader debate about modern dating norms rather than a single guest's opinion.
Together, the three clips track a single extended conversation that moves from Handler's tour and her self-appointed matchmaking role into a wider group discussion on dating culture, with Bertinelli's presence as guest host giving the roundtable segments a different dynamic than a typical one-on-one interview.
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