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Dos and Don’ts to Keep in Mind When Dating: How to Kill It on a First Meet

By Shirley Goldberg October 13, 2022 Dating

I remember my first ever online-booked meet. I can still picture walking up to the door of the restaurant and pulling it open.

It was late afternoon, and the sun blinded me for a moment. A few guys at the bar swiveled around on their barstools to check out the newcomer. One by one, they turned back. All except the man in the pink shirt.

It doesn’t matter that our first meet was our last. What matters is that only after meeting in person will you know if you’d like to see him again.

And, in case you were wondering if emailing, texting, and talking on the phone count… They don’t.

I’ve met many men since that first time, and let me assure you – yes, it gets easier.

One thing that doesn’t change, though, is the combination of excitement mixed with nausea. Why? You’ve been emailing. He commented on those great photos of you in Montmartre, your favorite Paris neighborhood. He told you the story about his grandson’s meltdown in Walmart. He thinks you’re cute.

You think you know him.

But… You don’t.

Whether you’re a newbie dater, or you’ve been dating for a while, here are some tips on how to be your best on your first meet.

And what not to do.

It’s All in Your Mind

An open mind is a wonderful thing to tag along with you on that first meet. It tends to protect you from an overactive sense of entitlement.

Entitlement thinking is not beneficial to your psyche. Let’s stop a moment and think about what you’re entitled to.

You’re entitled to someone who is kind and has values that match yours. And you’ll decide, upon meeting, if you’d like to get to know the gentleman better. Yes, you’re entitled to that, and so is he.

Be cautious about thinking you deserve tall with hair, no bellies, please, and financially well-endowed, thank you.

That’s going over the line into the kind of entitlement that will hold you back in your search. I know because I used to have a list.

One example from my list? Go ahead and laugh.

I wasn’t interested in anyone with typos in his profile. I thought that writing well translated to articulate, fun and super smart. A Norman Mailer/Jeff Bridges type. Once I started dating, it became obvious that a profile is a tiny piece of the whole man.

Compatibility is king. He may love flea markets, live theatre and Diana Krall as much as you do. Or a little rumba and a happy hour.

So, smile. Ask a question or two.


Having an open mind means you approach your meet knowing you will have fun. It means not deciding he’s too short before hello. Not blowing it with a fixed idea of how he should dress, down to his brand of loafers or his rolled-up jeans. Sure, that’s a dorky look, but give him a chance.

And while I’m on the subject, please save the molded-to-the body top for later, when you know him better. You don’t want to send the wrong message.

Here’s one last expectation to avoid. If you’re meeting for a drink, don’t hint around for dinner.

And if you’re meeting for dinner, don’t have inappropriate expectations. The French waiter and the stellar bottle of Pinot Noir may come later. This is a first meet, not an anniversary.

“I want to know she likes me for who I am,” says a longtime male friend. “So, I never do dinner for a first meet.”


Lots of folks leave their manners in the dumpster when it comes to internet dating. You’re not one of those, so:

  • Be an easy meet, willing to drive half way if he lives in a far-off town. Many men will offer to do most of the driving.
  • Be on time but be sure you have his cell phone number in case you’re caught in traffic.
  • Ask questions, show interest in the person you’re meeting.
  • Stop at nosy.
  • Be careful about ‘measuring’ the man too soon.

A first meet is not the time to ask if he’s got an ex-wife to support, or if he owns his house, or if he’s taken that pricey Alaskan cruise you read about. Unless this topic comes up naturally in conversation, he’ll know you’re probing into his finances.

A male friend of mine works for a company that invents and sells new devices for surgeons. He’ll never forget the woman who, on a first meet, asked, “What does a man in your profession make?”

He changed the subject and didn’t call her again.

Go gently into that first meet. You’ll have a much nicer time.

Have Fun

You’ll enjoy many meets. The keyword here is ‘enjoy.’

Smile, keep the conversation light and be genuine. You’re on a first meet to have fun and get a second meet.

Now, a second meet is called a date.

And remember, it only takes one.

One man to click.

Let’s Have a Conversation:

Tell us about a first meet you remember vividly. Did your meet say something to put you at ease, and if so, what was it? What would be your advice to someone facing their first online-booked meet?

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Kathy Pierce

Great article and runs true to form. I like to think of a first meet as I would if we were meeting at a social event and the type of conversation you might have with a new stranger encountered there.

Shirley Goldberg

Yes, but perhaps with a tad more pressure. A meet is a date, after all, much as I’d like to pretend it isn’t.

I’ll admit to distinguishing between “dates” and “meets.”

Peg Doyle

I’d add a few things to this great advice you gave. Be careful about where you meet. Make sure someone knows where you are and make a plan to call them when you leave your date, giving an estimate of when they should expect to hear from you. Don’t give your address or even your phone number to the person before you meet in person just in case they are off base And don’t worry about looking fabulous, just be your real self. Why try to be anything other than that? Feel great about who you are

Shirley Goldberg

Safety is always first. I didn’t even give out my last name on a first meet.
And I always wear something that makes me feel fabulous.

The Author

Shirley Goldberg is the author of Middle Ageish and Eat Your Heart Out, both romantic women’s fiction with seasoned characters. Her website,, offers a humorous look at living single and dating in mid life. Shirley’s friends nag her to tell them which stories are true in her novels.

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