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Navigating conversation during a date can be hard. It’s difficult to tell how fun and open your date is about things, what he or she would be guarded about, and what’s just a total taboo topic for that person. What you have to do is dance around certain subjects. It’s romantic boxing. You don’t go immediately for the right hook–you have to set up your heavy hand with the jab, and usually for several rounds before ever attempting it. So here are three jabs, three innocent questions that won’t make it sound like you’re prying, which can still result in some enlightening answers.
1. Who’s your favorite player?
Many girls will try to tell you they’re into sports, and they’ll usually name a sport specifically. “I’m a huge NBA fan,” she might say. The biggest mistake you can make here is asking what team she supports. Most people can spout off the names of teams pretty easily, despite having never watched a single game. Instead, ask her who her favorite player is, and then have the “Why?” chambered and ready to go. Sure, maybe she really does like Kobe and can list his playoff stats and tell you the number of game-winning shots he’s made. Or, more likely, she’s a bandwagon Lakers fan who probably didn’t even know Kobe was hurt all of last season and probably thinks he’ll be in the league five years from now. But every now and then, you’ll meet a girl who will tell you she loves Tim Duncan because she thinks San Antonio plays the most beautiful basketball in the league, and because she also appreciates his professionalism. I’ll obviously be immediately against her for being a fucking Spurs fan, but at least I can appreciate the sentiment.
2. What’s the most embarrassing thing that’s ever happened to you?
This is a relatively benign question, because it allows the person answering to set the tone for what it really means. She could talk about being called out by her boss in front of everyone in the office for spelling a certain word incorrectly all 34 times she used it in her report, which means she’s either dumb or she hates her job too much to notice the squiggly red lines under her words. She could also talk about an ex showing up at a bar while she was in the middle of a date and how she handled it, which gives you a lot of insight into her dating history. However, the king of all of them is the embarrassing sex story. Every bit of that anecdote will be useful. If it’s embarrassing because of something the guy did, then you know what to avoid in the off chance the two of you make it to the boudoir. If it’s something she did, then you know that she’s fun and open about her sexuality, and also that she’s self-deprecating enough to tell that story to you.
3. Have you ever been to Vegas?
Vegas is many things to many people. For some, it’s a family vacation, where you go to the the corporate hotels, theme parks, and magic shows. Others go for the club lifestyle and roll the dice on the prospect that the cocaine they buy from the dude in the silk shirt with the dragon on it is actually going to be good this time. Others are dumbasses who have convinced themselves that they’re smart enough to be professional gamblers and they chalk up their losses to bad luck. The one thing that brings everyone together is that everyone who goes to Vegas comes away with a story to tell. If you ask a girl if she’s ever been to Vegas, she’s immediately going to launch into her story. She might talk about going for a bachelorette party where they had a couple drinks, danced for a few hours, and then went to bed early so they could get to Celine on time the next day. That tells you she’s not super adventurous, or at the very least, that you probably aren’t getting laid tonight. On the other hand, if she talks about showing up to Tao in stilettos with her girlfriends, partying with C-list rappers at their table, and she vaguely alludes to hooking up with one of them, you know two things: she’s down for a good time, and she probably got an STD from Carrot Top.