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“Whether it was a boss in a previous job, a mentor, or a relative, asking your date about their role model(s) lets you sit back and listen as someone talks about someone who’s meaningful in their life,” Spira says.“Plus, you’ll see how it carved out the foundation of who they are today.”A lot of people have passion projects that they do for free, so now’s your chance to see what your date does in their spare time — and what they’d do as a job for free.
“Helping your date think about their fun vacations will put a smile on their face, and you’ll learn if they’re a sun worshipper, if they prefer to go museum-hopping in other cities, and so on,” Spira says. “All too often, people make the mistake of complimenting someone’s obvious physical good looks,” Carmelia Ray, matchmaker, online dating expert, and dating coach, tells Bustle.
However, you can also ask them not to choose an answer like “errands.” “Overall, it’s a fun way to peek into your date’s day-to-day lifestyle,” Edwards says.