First dates can be nerve-wracking, and sometimes, the wrong joke can turn a promising evening into an awkward disaster. But who says you can’t have a little fun while learning what not to say? Here’s a collection of first date jokes that walk the fine line between hilarious and “please never say this.”
First Date Fails: Jokes You Should Probably Avoid
While humor is a great icebreaker, some jokes might leave your date questioning your life choices. Here are some cringe-worthy (but funny) lines that should never make it into your first-date conversation—unless you’re aiming for an early exit!
- “Don’t worry, my last date said I’m way less creepy in person than online.”
- “I brought a list of exes for you to avoid. Want to add your name now or later?”
- “My therapist says I shouldn’t trauma-dump, so… how’s your childhood?”
- “If this doesn’t work out, my mom said she’ll set me up with her coworker’s daughter.”
- “I love your vibe! It’s giving ‘probably won’t ghost me.’”
- “I Googled you. Just kidding… unless?”
- “You remind me of my cat—mysterious, unpredictable, and kinda judgey.”
- “I don’t believe in astrology, but I do believe in background checks.”
- “I’m not a stalker, I just have a really good memory for details… like your address.”
- “If we get married, do you want a summer or winter wedding? Asking for a friend.”
- “I usually don’t make it past the first date, so this is already going great!”
- “I hope you like kids because I still sleep with a nightlight.”
- “My last relationship ended because I laughed at my own jokes too much. Want to test that theory?”
- “I’m really good at reading people. For example, you’re regretting this right now.”
- “I promise I’m fun at parties—if you consider ‘explaining Bitcoin for an hour’ fun.”
- “I don’t mean to brag, but my mom thinks I’m a catch.”
- “Do you believe in love at first swipe, or should I unmatch and try again?”
- “I’d offer to split the bill, but my wallet’s in my other pants… at home… in a different city.”
- “I’m not saying I’m desperate, but I did bring a ring… just in case.”
- “If you leave early, can I at least keep your fries?”
Why These First Date Jokes Are a Risky Move
While these jokes might get a laugh in the right context, first dates are all about first impressions. A poorly timed or overly edgy joke can send the wrong message. The key is to keep things light, playful, and not make your date question their safety.
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