My Cringe-Worthy Dating History
Back when I started dating seriously around 2018, I kept messing up without knowing why. Girls would ghost me after 2-3 dates, and I couldn’t figure out what went wrong. So I decided to track patterns by journaling every date for six months.
First big screwup happened with Sarah, this barista I really liked. Planned this fancy dinner date – made reservations at some overpriced French place. Showed up wearing a stiff suit while she came in jeans. Felt totally mismatched immediately. Spent whole dinner nervously rambling about my coding job when she clearly wanted to talk about hiking. Never texted back after I paid the huge bill.
Then there was Lisa, who actually agreed to a second date. Took her bowling which started okay, but then I panicked when things got quiet and started grilling her about ex-boyfriends. Like actually asked “So why’d your last relationship fail?” Total mood killer. Saw her physically tense up before making an excuse to leave early.
Breaking Down My Dumbest Moves
When I reviewed my journal, three mistakes kept popping up:
- Over-planning dates like some military operation instead of keeping it chill
- Talking about myself non-stop like a podcast host interviewing himself
- Getting clingy way too fast – sending good morning texts after one dang date
But the biggest realization came when I showed my notes to my female friends. They pointed out stuff I never considered. Like how I’d always pick places near my apartment “for convenience” (which screamed creepy), or how I’d “accidentally” brush their hands too much during conversations.
My Experimental Fix Phase
Decided to test new approaches for 90 days. Ground rules were simple:
- Always start with low-pressure coffee dates
- Let them pick location half the time
- Listen more than talk – kept mental timer for 70/30 listening ratio
First test run with Mia started rocky because I defaulted to old habits. Caught myself doing the “me monologue” about cryptocurrency but stopped mid-sentence to ask about her dog. Saw immediate change in her expression – shoulders relaxed, she started smiling. Ended up walking around the park for two extra hours just chatting.
Another experiment involved admitting awkwardness upfront. With Priya, straight up said “First dates make me nervous so I might talk nonsense.” She actually thanked me for being honest, and it killed the tension completely.
What Finally Clicked
After three months of conscious effort, my success rate flipped. Got five third dates in a row instead of constant ghosting. Key takeaways:
- Pretending to be smooth backfires – owning nervousness builds trust
- Planned “perfect dates” feel like job interviews – messy conversations create real connections
- Attention > perfection – remembering small details beats grand gestures
Biggest mindset shift? Stopped treating dating like some game to win. When I focused on enjoying their company rather than impressing them, everything got easier. Still make mistakes sometimes, but now I laugh about it instead of obsessing. Dating’s way more fun when you’re not overthinking every move.
