Matthew (DT145)

CEO of watchgang.com — gives away a Rolex every Friday. Sponsored the episode; conducted Rolex giveaways for viewers via YouTube comments after show. Owns a boxing gym in Los Angeles. Engaged throughout on topics of pornography, dating, age gaps, and prenups. Provided measured take on prenups as risk management tool. Was a primary voice on the economics/practical side of dating debates.

Returning guest (also appeared DT#145). Divorced after 8-year marriage (2 kids). Initiated the divorce due to fighting in front of kids. Met ex-wife on an airplane; she was a hair stylist moving to LA; got pregnant ~2 months in. Paid 4 years of alimony; ex-wife became a millionaire from the divorce settlement. Would not remarry under current California divorce laws. Self-rates looks: 7/10 (currently 5 due to weight; potential 8 if in peak shape/ripped). Does not date for marriage; dates for connection/compatibility without needing a wife. Agnostic (was Christian; now on the fence). Plans special watchgang.com giveaway for Whatever viewers on following Tuesday episode.