Ask Wendy

Why Can’t I Get Past Date #1?

Friday, November 23, 2018
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Hey Wendy,

I’m now 72 years old but people think I’m 60. I’m young at heart, 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?

Louise C. – Saratoga, California

Hey Louise,

I wish I could be there with you to see what’s going on and give you the why!  Why, why, why aren’t you making it past the first date? Since you can’t put me in your pocket and take me with you, I’ll start by asking you three questions:

Is there 100% truth in advertising? Are you the exact same person you present in the words and images on your online profile? 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 .

Are you treading in dangerous territory? If you’re hanging out for hours, 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.

Are you bringing substance? Fun is awesome! You want to bring lightness and spark to a date, but are you bringing more than that? Are you expressing the deeper sides of you? Not the heavy sides—the deeper sides. Are you showing your dates your personality’s unique flavor, what you care about, how you spend your time, and what really matters to you?

Sometimes when we don’t get second dates it’s because of the cotton candy phenomenon: all fluff and no substance.

Louise, if you’re doing everything right—advertising who you really are, keeping the rough stuff for another time when you know each other better, and not shying away from expressing your core essence—then if they’re not following up with date number two, they’re doing you a favor. They’re not for you, and they’re just getting out of your way to make room for your person to come into your life. Don’t stop, he’s going to show up.

Good luck out there!

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