3 Reasons Why You Can’t Get Past the First Date

Wendy Newman
3 min readFeb 16, 2021
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Ask Wendy: Dating, Sex & Relationship Advice for the Bold

Hey Wendy,

I’m 45 years old but people think I’m 30. I’m youthful and I exercise regularly. I have quite a few men contacting me, but I don’t seem to get past the first date. We have lively, fun conversations, and sometimes we’re even together for three hours. What’s my problem?

Lena C.

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Hey Louise,

I wish I could be there with you to see what’s going on and give you the why!

Since you can’t put me in your pocket and take me with you, I’ll start by asking you three questions:

100% truth in advertising

Are you advertising yourself as the real you?

The person you present in the words and images on your online profile needs to be who you actually are.

Are your photos current? And when I say current, I mean taken-within-the-last-six-months current.

Are there close-ups and full-body shots that accurately portray what you look like right this second?

Are you stretching it a little when it comes to stats like your age or body type?

In the case of online dating, honesty really is the best policy. Look over your profile, and if you’re willing, let a friend also take a glance and make any needed updates.

Dangerous Territory

Are you treading in dangerous territory? If you’re hanging out for hours on end, we can all assume you’re entertaining and fun, but are you sprinkling in some heavy, not-first-date topics too?

Are you (over)sharing your entire life story that includes the messy details of all your past relationships?

Are you telling him he seems beyond amazing and you hope to be exclusive with him soon?

Those are just a few examples in a long list that will kill the chance at a second date.

The Cotton Candy Phenomenon

Are you bringing substance?

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Wendy Newman

Dating, Sex & Relationship Expert and Author of 121 First Dates (Simon & Schuster). Over 80,000 women trust Wendy’s advice, tools, & experience. WendySpeaks.com