I Can’t Get Past My First Date, Help!

Ask Wendy: Dating, Sex & Relationship Advice for the Bold

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 pretty sure it’s me. Could you give me advice on what to say (or not say) on a first date to make it to a second one?

Terry D.

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Hey Terry,

I’m curious to know what your top 3 date topics are…

Do you start with, “My ex-husband is the biggest asshole I know”?

Or, “So here’s a fascinating thing I learned about you when I Googled you”?

Terry, do you show him photos of your taxidermied bird collection?

Without knowing what you say, I can only guess based on what I’ve heard other women say over the past two decades, so here I go, guessing.

#1 Most Common Mistake Women Make…

We tailor our questions to vet him.

Many of us treat dating like we’re the director of a film and we’re casting for the lead role of…

boyfriend/husband/partner/father-of-my-children.

If this is you, please kindly knock it off.

The “interview” is a huge turnoff.

You can’t vet him — he’s a stranger.

And asking qualifying questions pushes guys away.

You’re not going to get any of the information you truly need out of him in the first two hours anyway.

First Date Questions for Winning at Dating to Find Love

Instead of the interview questions, try some of these:

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

“What do you love about your life?”

“Who’s your favorite underdog and why?”

“What are you really good at?”

“How was your week?”

These ‘get to know you’ questions are positive and leave plenty of room 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?” well, that’s some solid sorting information for you right there.

Blowing a First Date

Another turnoff is talking about timelines. I know more than one woman who has said on a first date, “I want to be married and have babies within the next year.” While that might be true, she’s sharing with a total stranger. At worst, he’ll find this statement scary and at best, he’ll think she’s showing a serious lack of good judgment.

Winning at a First Date

Here’s the big secret to a successful first date: If you show up on your date as yourself (not who you think he wants you to be), and you learn a few things that are unique about him, and you share a few unique things about you too, you’ve done your job, regardless of the outcome.

Snappy comebacks and witty repartee can be fun, but if that’s not who you naturally are, don’t try and bust them out. And even if that is who you are, a little goes a long way — be willing to get a little vulnerable and share yourself. Nothing good ever happens in romance without a little vulnerability.

A Good Date

A good date is hanging out and getting to know what matters to a total stranger. Learn something new, and whether there’s chemistry or not, hopefully, you’ve both had a nice time.

If you want to do a deep-dive on how to succeed at dating to find love, grab my DIY workshop, Ready for Love. You can download the audios, or watch the videos and I’ll cover absolutely everything you need to be successful in finding love.

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

Wendy Newman is the author of 121 First Dates. She’s a dating, sex, and relationship expert who’s led hundreds of workshops and revolutionized the lives of over 70,000+ women internationally.

You can send a question to the column via email: [email protected]

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This post was previously published on medium.com.

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