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0; Genuinely Interesting Questions For You To Ask Your Next Date. It’s really, REALLY attractive when people ask well thought out questions on a first date that at least give the illusion that they want to know you better—not just know where you went to college and what your worst OkCupid story is. Casual– these questions are perfect for a first or second date or networking event.. A little more personal– these questions are good to ask someone you already know but want to know are perfect for friends or a guy you’ve been dating for a little while. Going deep– These questions are meant for people you already know pretty well, close friends or a significant other Questions to ask someone on an online dating site - Is the number one destination for online dating with more marriages than any other dating or personals site. Join the leader in footing services and find a date today. Join and search! Register and search over 40 million singles: chat. · The excitement of meeting someone new is beyond the world. The nervousness, the awkwardness, the adrenaline rushes and the accidental touches - your first dates are full of mixed feelings. When you first start dating someone, you want to talk for hours and know all you can about the other person. · How To Have A Conversation On A Dating App (Hint: It’s Not That Hard) I consider myself someone who can talk about a variety of subjects, with a variety of people. ... Ask questions ... joe jonas hailee steinfeld dating If you just started online dating, or perhaps you’re a veteran, there are a few important questions to ask your potential date so you can more easily determine if he or she is a suitable match for you. Below find a list of Dating with Dignity’s top five questions you should ask an online date.