Before Erin and I went on our Skype dates, Glamour set us up on a conference call with dating expert Rachel Greenwald. One thing she really stressed was the importance of coming up with a few icebreaker questions to get the conversational ball rolling. I was skeptical—aren't icebreakers kinda corny? But Rachel made a compelling argument that it's better cheesy questions are ultimately more effective than tired demographic inquiries like "How many siblings do you have?" and "Do you have any life-threatening food allergies?" So I came up with a few icebreakers in advance and, lo and behold, they totally worked! Now I'm asking every girl I meet silly questions. Here are a few or my favorites:
1. If you were a character on Friends, which one would you be?
I asked this question to each of my Skype dates, and each one of them gave me a different answer (Julie, who identifies with the duck, wins the "Most Creative Answer" award). There's only one wrong answer to this question: Ugly Naked Guy.
2. What’s your favorite song to sing in the shower?
Everyone hates the question "What kind of music are you into?" because you have to rack your brain to remember the weird name of whatever band Pitchfork is into right now. But asking people for their shower playlist allows them to reveal their guilty pleasures. When I'm rockin' the loofah mic, I go for old soul jams like "Tracks of My Tears" or a Phantom of the Opera medley. Top 10 Breakup Songs Of 2008
3. What was your favorite book when you were young?
I don't know about you, but I light up at the mere mention of The BFG or Harriet the Spy. And hearing what type of books a girl was into can be very revealing—did she read The Babysitters Club or the Tillerman Cycle (or both)? This question always leads to awesome nostalgia freak-outs.
4. What is the weirdest thing that ever happened to you?
Everyone has at least one story about a seriously weird experience. Maybe they got stuck on a broken elevator with Weird Al Yankovic. Maybe they dated the President of the Weird Science Fan Club. Maybe they played one of the Weird Sisters in an all-nude version of Macbeth. What's my weirdest experience? Probably going on those video dates. Get Guys Begging For A Second Date: Here's How
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