Five conversation starters

By Brienne Walsh

We all know how the drill goes. You connect with someone on MeetMoi, and choose somewhere to meet. When you arrive, you ask all of the expected questions. Then, once you’ve finished your drink, you’ve run out of things to discuss. You awkwardly sit there, wishing you could go home and watch your DVR recording of Mad Men. Or at the very least, check to see if you got any text messages on your iPhone.

But not every blind date needs to feel like a job interview. We’ve put together a list of five questions that will get a conversation started in no time…or at least lead to a second drink.

1.   What’s the craziest thing you did in college?

The guy sitting before you may look like a buttoned-up investment banker. But maybe he traveled by himself through Tanzania, or delivered donuts in his underwear in the library during finals. Crazy doesn’t have to be a warning sign. Instead, it can be an indication that the guy you’re with likes to think out of the box—and might be interested in sharing his wild side with you.

2.   What’s the last movie that you loved?

Movies can tell a lot about a person. For instance, for you, the Hangover 2 might have been the greatest disappointment of 2011, while for your date, it was the funniest movie he saw all year…if not in his entire life. Or, you may the type of girl who loves a Godard retrospect, while your date falls asleep in anything except for a thriller starring Shia LaBeouf. Either way, the question conversation usually leads to a playful debate.

3.   What do you when you wake up on a free Saturday morning?

What someone chooses to do on a leisure day is usually very telling of their priorities. If he would spend the day having a boozy brunch with friends, and you would spend it biking alone, then maybe he’s an extrovert and you’re an introvert. That would be tricky in a long-term relationship, especially if he wants a girlfriend as a sidekick, and you want a boyfriend who gives you space. If nothing else, the question might give you some ideas of fun things to do on your next empty weekend.

4.   Where is your dream place to travel?

They say that traveling together can make or break a couple. If you can’t face the unknown together on a trip, then how will you ever deal when traumatic situations arise in real life? A big part of traveling well is being on the same page about where to go. If your dream is to trek from Kathmandu to Mount Everest, and he wants to go lie in front of a resort on a beach, then you’ll never be satisfied with your precious vacation time together.

5.   If you were stuck in a room for ten years with either Donald Trump or Tim Tebow, who would you choose? (Or any other hypothetical question.)

Asking hypothetical questions can be a great way to determine whether or not someone has a sense of humor. For instance, if you ask a date, “If I was 100% perfect for you, but I insisted on wearing a helmet when I was driving a car, would you still date me?” And he stares at you with a blank face, he’s probably not the guy for you.

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