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I once got an opening message reading, “Do you like sex?” Hint: That’s not a good question to ask a woman online (or ever, really). Stay away from sex talk until you’ve built up a rapport with a girl.

They say age is just a number, but it’s always nice to know how old someone is. Do they like sleeping in late and watching Saturday morning cartoons? This is a great way to hear a sentimental story from them about their first love, it’s sweet.

#48 When was your last relationship, and how long did it last?

He noticed details, remembered names, and never seemed at a loss for words. ” And I thought for a moment before answering, “You ask good questions.” He thought I was joking, but I was completely sincere.

#33 What’s the most embarrassing thing that’s ever happened to you? Maybe it’s watching their sister graduate university or their parents buying a house. This is a great way to see how their relationships are with immediate family members. Or in other words, are you an optimist or a pessimist? This question reveals what a potential partner values.

Well, we all have a horrible first date story, so you might as well share them and laugh together. If you’re a real book worm, and the last book they read was a few years back, well, it might not be a match. This time, they should think about what type of partner they want. [Read: 8 important questions you have to ask on a speed date] #37 What’s your proudest moment? This sounds weird, but if they don’t do anything, well, their anger just builds inside of them. Maybe it is a secret love for the Hallmark channel. How to be witty and win over anyone] #40 Who are you closest to in your family? #42 If you won the lottery, what is the first thing you’d buy?

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