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There's this weird fine line right before oversharing, a certain amount of time past the initial pleasantries on a first date where it's actually really awesome to bring up the serious things about yourself, and if done the right way breaks through the ice, inviting an actual sort of intimacy to exist and inviting the other person to actually tell you about themselves. Don't go too crazy though. You can kind of just say "fuck it" and be really honest. People will be surprised and you will usually get a second date.
Sep 17, 2024

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I’m pretty sure you’re supposed to say, “Good and you?” when someone asks, “How are you doing?” Not me. I love taking this opportunity to honestly unload exactly where I’m at on the ever swinging pendulum that is my constantly shifting emotional/psychological/spiritual state. Try being completely transparent next time someone cracks open this door to a potentially true human connection.
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Bring up a fun fact, it breaks the ice and gets a conversation rolling. If that doesn’t work, being honest also works. Addressing the awkwardness head on really helps remove the tension.
May 28, 2025
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If I run out of questions to ask or things to say on a date its easier to just say… I cant think of any more questions, rather than forcing something. You can always find another thing to do or! or just sit in silence without expectations. Awkward silence isn't awkward if your both know the reason why its silent 👍
May 27, 2025

Top Recs from @jude

Going to restaurants alone and phoneless! Being in traffic! Having your train be stuck on the subway! Being incredibly early to things! Waiting is an extremely exciting activity if you let it be. Just sitting around and noticing things, noticing your body, noticing how you feel
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Further concretizing your understanding of someone and letting them be excited > allowing them to feel sheepish
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maybe I won't get my car back from the tow pound. maybe it's just a distraction from the important things in life.
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