Ask Wendy

How Did I Blow My First Date?

August 30, 2016
Hey Wendy,

It seems like I’m screwing up dating lately. When I first meet the guy, he likes me but by the end of the date, he’s out. Some of them say, “It’s not you, it’s me” but I’m guessing it’s me. Could you give me advice on what to say (or not say) on a first date to make them want another one?

Terry D. — Santa Anna, CA

Hey Terry,

I’m curious to know what your top 3 date topics are. Do any of them start with, “My ex husband is the biggest asshole I know.” or “Hey, fascinating thing I learned about you when I Googled you!” or “Want to see photos of my stuffed bird collection?” Without knowing what you say, I can only go by what I hear from most women.

The #1 most common mistake we women make is we ask questions to vet him. Many of us treat dating like we’re the director and we’re auditioning for the lead role of… boyfriend/husband/partner/father-of-my-children.

If this is you, Blowing It, you can’t vet him – he’s a stranger. And asking qualification questions pushes men away. Also, you’re not going to get any of the information you truly need out of him in the first two hours anyway. So instead of the interview questions we love so much, try some of these:

“What are you looking forward to that’s coming up in your life?”

“What do you love about your life?”

“Who’s your favorite underdog and why?”

“What are you really good at?”

These “get to know you” questions are positive and have the ability to go from shallow small talk to deep, meaningful conversations. If he’s keeping it shallow, that’s something to note. It’s not a red flag, but it’s more like a pink post-it note (tag it there and check back on it later.) If he doesn’t have an answer for, “What do you love about your life?” that’s some stellar sorting information for you right there.

Blowing It, if you show up on your date as yourself, and you learn a few things that are unique about this total stranger, and you let him learn a few unique things about you too, you’ve done your job, regardless of the outcome.

Snappy comebacks and witty repartee can be fun and all, but if that’s not who you naturally are, don’t try and bust them out. You just be you. Let him know what makes you unique. Try not to talk in timelines — and for the love of God, do not tell him you want to be married, and have babies in the next 9 months; he’s a total stranger, and that will be scary and show serious lack of good judgment.

Good luck, Blowing It, I hope your next few dates are a string of victories!




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