In this laugh-out-loud performance, Tommy Brennan dives headfirst into the chaos of relationships, revealing the hilarious (and sometimes painful) truths that come with being a boyfriend in the 21st century. In "How to Make Your Girlfriend Cry," Brennan unpacks the innocent moments that turn into emotional disasters—and the clueless things guys do without even realizing.

With quick wit, perfectly timed pauses, and a tone that screams, “I swear I meant well,” Tommy walks us through miscommunications, dating disasters, and the bizarre things that make relationships so difficult and so entertaining. It’s comedy rooted in truth—relatable, raw, and ridiculously funny.

Whether you’re single, dating, or deep into a committed relationship, this stand-up set will have you laughing (and maybe rethinking your last argument). Press play and prepare to cringe, chuckle, and completely relate.

#tommybrennan #standupcomedy #relationshipcomedy #funnyrelationships #datinghumor #relatablecomedy #couplegoalsgonewrong #comedyspecial #laughoutloud #modernrelationships #relationshipstruggles #funnytruths #comedylovers #emotionaldamage #howtomakehercry

Comedians: Tommy Brennan, Nate Bargatze, Sam Morril, Taylor Tomlinson, Mark Normand, Ali Wong, Tom Segura, Nikki Glaser, Trevor Wallace, Chris D’Elia, Whitney Cummings, John Mulaney, Iliza Shlesinger, Pete Holmes, Andrew Schulz

Advertising Inquiries: https://redcircle.com/brands

Privacy & Opt-Out: https://redcircle.com/privacy