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Inquire about anything from your date's first crush to his most awkward experience in high school.

Be prepared to share details of your childhood as well, and determine what kinds of information you will be comfortable sharing.

Don't make them pick All right, so maybe you're out with the an OG Airbnb employee, or maybe you're out with someone who has no idea what a startup is, but I think this question is fun because it's pretty much like asking: "What's an app that doesn't exist that you wish did? Who knows, you could be on a date with a VC person who actually wants to fund your idea.

If you're out for drinks and your date orders a Manhattan, ask them if that's their favorite cocktail. (If you're not drinking, you can also ask about the other D word, dinner...best restaurant they've ever been to, favorite food, whatever.)Again, this is a total go-to, but everyone loves talking about where they are from.I think asking them the best or worst part about growing up in Nashville or Miami or wherever makes the question more specific and allows you to learn more about them, too.Everyone loves to humblebrag about their sweet vacations." Hopefully, your date like their friends and will be happy to chat about them.

This question will probably allow you to get into where you each hang out in the place that you live, and get a feel for what mutual interests you might have.And if your date shoots you down with an "I haven't been anywhere in forever" rather than chime in about your bomb trip to Machu Picchu, ask them where the top place on their travel list is.Pro tip: This works on a bad first date, too, because you get to escape the setting in your mind for a moment.Effective communication is an essential component of engaging in discussions with others, and skills such as active listening, paying attention to nonverbal cues and remaining focused on what your partner says enhance discussions, notes Psych Central CEO and founder John M. Discuss goals for various aspects of life, such as romance, career and family.This kind of discussion gives you both an idea about each other's short- and long-term plans, and allows the two of you to determine whether or not your plans are in alignment.other dates or exes on a first date, but I feel like acknowledging how badly things could go together is a great icebreaker.