First Date Conversation Survival Guide



Fast-forwarding through the dating app swipes, the terrible pickup line that somehow worked, or the awkward first encounter at the bar last weekend when you mustered enough alcohol-born courage to ask Emily out, we arrive at your latest (possibly last) first date.

You decided on drinks with the potential for dinner afterward because you’re hopeful but smart about not committing to a full date right away. It’s a Thursday night, so anything could happen as long as you’re asleep by 1 am; after all, it is a “school night.” You see her at the bar. She’s just as attractive as you remember from either her Bumble profile or that dark bar - both equally misleading - and she is now sitting across from you at a high-top table. You’re looking into each other’s eyes. Inside you’re psyched about her saying yes to the date because you haven’t put yourself out there in a while and she looks like a catch. Then, the panic sets in. You have no idea what to talk about. “The bar conversation/tinder IMs came so easily!” you think to yourself. This is your chance to make a real impression, but you feel yourself freezing up. “So, are you from around here?” said the scared little boy.

Sound familiar? This happens more often than most would like to admit, and it’s our goal to ensure that it doesn’t ruin your date with the future Mrs. Right. A gentleman should always be prepared, and the first date is no exception. To stop these first date freeze outs, we sat down and thought about some great questions that have landed favorably in our lives - questions that open up the conversation in the event that any lulls may arise. These aren’t your typical work team-building event icebreakers. We call it the First Date Conversation Survival Guide. Enjoy.

Pro Tip: Make sure you’ve thought about your answers to these questions because she is more than likely going to ask you right back.

If you were going to be sent to an island all by yourself with just a cd player and 3 albums, which would you pick?
If you could live anywhere, where would you want to live? Why?
What was the most embarrassing thing you’ve done on a date?
What is your worst first date experience? (hopefully not this one)
What is the most embarrassing thing that’s happened to you at work?
If you were to lose your dominant hand and had to replace it with a household utensil or object, what would it be?
What was your first AIM screen name?
If you were gifted $10 million and couldn’t spend it on yourself, how would you spend it?

Seeing that you don’t ruin the date with odd gestures, what other first date topics are your go tos? Help a gent out and share below.