5 Great First Date Convo Starters

I have no idea how many first dates I've been on. 40? 50? 100? No idea. But I still get nervous every time, dreading the awkward silences after the good to meet you's fade away.

Now, I'm a journalist, so it's my job to ask questions. I know how to ask about your background, where you're from, and where you see yourself in 10 years. And then, back in college, I volunteered on a phone crisis hotline, where I learned to ask questions like so, how depressed are you? and tell me more about how you want to kill yourself? without flinching. I am good at asking the hard questions, but these don't necessarily make great first date fodder.

So, I've come up with a cheat sheet of sorts of first date questions that work for me. I like a blend of odd and unexpected, questions that are open-ended and that do not sound like you're rattling off your resume. And-please-I'd love to hear yours, too!

What five websites do you visit every day? Love this one! This gives such great insight into the guy's personality-you can find out whether or not they're a news freak or a gossip hound, whether they love sports or Internet LolCats.

Favorite vacation ever? I like this one because I think it really shows how adventurous a guy is-do they like far-flung locales or is their favorite place the same rental at the beach every year?

Did you win any superlatives in high school? If not, what would you have gotten?
This one shows how other people see him, and it's a great way to segue into a discussion on what they were like as kids/how they experienced high school. Were they all about superlatives or did they think that was dumb? Were they the type of guy who should have won worst case of senioritis or were they the type of guy who won most likely to succeed? I think it's a fun way to find out what part of their personality THEY think is unique. Plus, then I get to slip in how I was voted most dramatic in high school-because, ideally, these are give and take questions that lead to a cool convo!

What gets you through the day at work/what's your guilty pleasure?
Everyone has one, and I like this one because it tightly focuses the question. I like knowing whether a guy loves his 3pm latte runs or can't function without a bag of M&M's on his desk. Plus, then it segues into whether or not he likes his job/how happy he is in the office, which I think is important in knowing his overall level of stress/happiness with life.

Sketchiest roommate situation?
In New York, everyone has at least one story, and people LOVE talking about them. He'll relax into telling the story, and you can quietly assess his social skills. Was his roommate a total neat freak, or was his nightmare roommate the guy who didn't clean up after himself? Did he think the roommate who went to bed at 10pm every night was creepy or did he cringe at the dude who rocked on his guitar at all hours? It gives a cool peek into his life (and helps you see if you and he might be compatible roomies somewhere down the road!)

Now, obviously, I'm not asking these one by one in a barrage of questions. But I LOVE having these up my sleeve so I can drop one when an awkward silence hits. What do you think? What do you ask?


43 Date Night Ideas
The Great Date Night Debate
Make Time for Two
Cheap Date Ideas
Get More on Love, Family & Fashion - Subscribe to Redbook & Save up to 82%!