Cyber-Dating Expert

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First Date Conversations – To Tell, or Not to Tell

Ask the Cyber-Dating Expert

I’m a believer in authenticity when it comes to dating. That means I believe you should tell your correct age, post recent photos, and be recognizable when you meet your date in person.

I also believe you should ration your information flow early on, so I find it disheartening to see dates with promise quickly end with no chance of a second date ever being put on the calendar.

Where am I going with this? Quite simply, you need to be prepared for your date. Before you leave the house, think about what you should and what you shouldn’t talk about. Think about what you’d tell a perspective boss to land your dream job, and what personal information shouldn’t make it to the interview. So without further digital ado, here are some dating tips and conversation topics to tell, and those that should quietly go to sleep with you at night alone.

1st Date Conversation Deal-Breakers Include:

  • The ex-factor – Too much talk about your relationship history.
  • The crazy ex-factor – Yes, every ex-wife or husband and ex-girlfriend or boyfriend were crazy. Can you elaborate? Please don’t.
  • Your divorce – Leave that to the attorneys. Your date isn’t your legal counsel.
  • Your therapist – We won’t give you sympathy on a first date, so leave your emotional problems for your next shrink session.
Conversation Starters Include:
  • How proud you are of your children. Don’t hide them from us. If you’re a great parent, we’d like to know.
  • Where you grew up and who inspired you.
  • Favorite vacation spots and cuisine.
  • Favorite musical acts or concerts you’ve seen or books you’ve read.
Now that you have the short list, I’ll share with you some details about a couple who met on a popular online dating site. Their first date fizzled out fast and made it to the Peril of the Week.

For starters upon meeting, the gentleman proceeded to tell the lady she didn’t look like her photos at all. While that’s a common problem and one of the biggest fears a man has when he’s making a dinner reservation for a blind date, it quite simply wasn’t the case. Her photos posted to her online dating profile were recent and every other man she dated in the past few months had remarked about how much she looked exactly like her photos. Some even said she looked better than her pictures.

This gentleman justified his comment and proceeded to tell her that he was formerly a professional photographer. He was an expert and he was quite certain that she didn’t look like her photos. He then proceeded to say that she was extremely photogenic, but in real life looked very plain. Are you laughing yet? He insulted an attractive woman who he was actually interested in by telling her she was plain.Flattery does go far, s0 why tell a woman on a first date that she looked like a plain Jane? It was simply insulting. Isn’t it better to say nothing and just enjoy the conversation?

Then he started the nervous interrogation about her previous marriage by saying,? “So who ended your marriage? You, or your husband?” Did it matter? No. She had been divorced for almost 10-years. It was old news and not first date conversation material. All that mattered was that her divorce was final and she was available to date. Her reply, with my coaching was “I don’t recall.”

Then he went down memory lane about his past and told her how he did LSD at Woodstock in 1969. Did she really need to know about his drug habit from 40 years ago? No, not really. Was he putting his best foot forward? Not at all.

Finally, he told her how crazy his ex-wife was and that she was bi-polar. As he started to talk about her manic-depression episodes, fortunately the alarm went off on her BlackBerry to let her know that the 2-hours in the parking meter had run out. She had 5 minutes to leave in order to avoid getting a parking ticket.

She gracefully thanked him for dinner and received a text message the next day telling her he had a great time and wanted to get together again. Remember, it’s a first date, not a therapy session. You may be nervous. After a few drinks, you might feel comfortable revealing all, but you’re making a first impression on someone you might spend the rest of your life with. If you think you shouldn’t tell a prospective boss about your days of doing LSD and bi-polar spouse to land your dream job, then you shouldn’t do the same with a woman or man you’re interested in dating.

Can you relate to this dating dilemma? Comments are welcome and we’d love it if you’d like us at and at

Julie Spira is the bestselling author of The Perils of Cyber-Dating: Confessions of a Hopeful Romantic Looking for Love Online. Visit her at for dating advice and to learn how to create an irresistible online dating profile.

Julie Spira is America's Top Online Dating Expert. She's an award-winning dating coach who's been helping singles find love online for 25+ years. Follow @JulieSpira on IG.

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