Online Dating

How You’re F***ing Up Your First Offline Dates

Gina Stewart

Written by: Gina Stewart

Gina Stewart

Gina is the owner of Expert Online Dating. As an online dating consultant, she helps men and women maximize their online dating experiences to get more dates. You can visit her website,, for more information or to contact her.

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Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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Online dating can be some work, so if you’ve gotten to the point where you’re actually meeting people, you don’t want to ruin your chances with some silly mistakes.

A friend of mine just had an online date with a man who had great potential.

He was smart and attractive and they had great conversation. However, he messed up on some key things, which left her uninterested in seeing him again.

When I asked my friend where her date wanted to meet her, she gave me the address of a Starbucks. Starbucks is a pretty standard meeting place for online dates, so that isn’t a big deal.

What the guy failed to realize was this Starbucks was inside a grocery store — without a place to sit and it closed at 8 p.m.

1. Do a little research when you suggest a place to meet. is a great asset.

If this guy had been early, or even on time, he would have made the same observations my friend discovered at the grocery store.

But since he was late, and she was the one to find all of this out, she suggested meeting at a restaurant a few doors down.

2. Be early.

Not just on time, but early. And never be late. It’s the gentlemanly thing to do.

Be early, find a spot to sit and send her a text that says where you are. Wait to order until she gets there.

These things will all help put her at ease and make you seem thoughtful, which will make it easier for her to enjoy her time with you.

If something unexpected should come up, like a spot being closed, you can be the problem solver.

When you are late, you send a message that you don’t value someone else’s time.

“These things will put her at

ease and make you seem thoughtful.”

My friend wasn’t thrilled at his tardiness and his lack of a plan, but she was there and wanted to make the most of it. They had a beer and a good conversation.

The nail in this guy’s coffin was what happened when the check came. He had good instincts to go for the check and she was polite enough to offer to split it. He said that wasn’t necessary and she didn’t object.

But the guy kept it going and said, “Well, you didn’t put up much of a fight,” inferring she should have tried harder to pay her way.

She was so put off by this comment that she grabbed the check and paid for his drink as well as her own. He didn’t put up any fight.

Gentlemen, I know women make just as much as men do now and there is going to be plenty of opportunities to navigate the financial waters of dating. However, on a first meeting…

3. Always pay for a woman’s $6 drink.

It can only make you look good. Any other arrangement doesn’t work in your favor.

And don’t make a comment about it. Act like you’re happy to pay because it allows you to be in her company. It will make her feel good.

Have you ever messed up meeting your online date? What would you do differently?

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