Joy of Missing Out (JOMO) Dating When You're "Too Successful" ft. Kristin Chen (Ex-CPO, Director of Product)
Mar 23, 2026
Kristin Chen, a former CPO/CEO turned advisor and career coach, shares wild dating lore from her tech-life: breakup contracts, a Hawaii date that looked like a job interview, and financial red flags. Short, sharp stories about control, insecurity, screening tactics, and why ambitious women face strange relationship patterns.
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Engagement After A Fast Burn Relationship
- Kristin described getting engaged after nine months with someone she'd known briefly from work and dating sporadically over three months.
- He moved in, she paid most expenses, and COVID delays stretched the relationship to three years before she broke the engagement.
Breakup Contract Demanding Half Her Home Costs
- Kristin received a bizarre breakup contract from her ex demanding half her mortgage, HOA and property tax as a payout.
- He framed ownership delusions and later tried legal threats after his startup failed and he grew jealous of her success.
Successful Women Often Attract Insecure Partners
- Kristin and Eric observed successful women often attract insecure or controlling partners who feel threatened by their success.
- Those men either try to be financially dependent or insist on traditional provider roles, producing recurring relationship conflicts.