Lost Password?

A password will be emailed to you. You will be able to change your password and other profile details once you have logged in.

Online Dating: Meeting a Guy for the First Time

meeting a man for a first date

by Tina Boomerina (Christina Gregoire)

Online dating is a lot of fun... if you have the right mindset. Of course, not all of the men you talk to online are exactly what you think (and hope) they will be. So, here are my tips for meeting a man from match.com or some other online dating site for the first time.

Safety and Online Dating

I met my husband on Match. So, I am NOT trying to scare you too much, but there are a few crazies out there.

Sure… you may be looking at a photo of a reasonably handsome man in his late 50’s, but for all you know, you’re talking to a bored nun in Guatemala… or a guy in prison for offing his wife. So, read the safety tips on Match. (I've put a link at the bottom of this article.)

online datingMost men are perfectly harmless, but here are the main rules:

1. Tell someone: Let someone know where you’re going, why you’re going, and when you expect to be back. (Actually, I never did this, but it’s a good idea.)

2. Meet the guy in a public place: Starbucks was my public area of choice. I always followed this rule and safety was just one of the reasons.

3. Make sure the man isn’t following you when you leave: Of course, if the guy is halfway intelligent, he can probably find you through your license plate. I’m not sure how to get around that problem. Any ideas?

Should You Go Out for Dinner or Drinks on a First Meetup?

After you’ve been chatting with some guy for a while and you’re ready to meet him in person, what do you do? It’s going to be a bit strange…I know. On the other hand, you don’t want to conjure up elaborate fantasies about a man who has half his teeth missing or who can’t afford to buy you a cup of coffee.

These rules will help you keep your sanity in the zany world of online dating:

1. No dinner dates: Don’t go out to dinner with a man you’ve never met. Hey, unless you’re so broke that your fridge is empty, why would you want to spend two hours with a man you may not like?

2. Keep it short: Tell the guy you only have 15 minutes to grab a cup of coffee with him. Then, if you and your blind date have chemistry, you can always stay longer to find out more about each other.

dating online3. No drinks: Don’t go out for a drink with a guy you’ve never even seen in person. What if you get a little too tipsy or he slips you a roofie and you wake up at his place?

4. Consider a drive-by date: This sounds a bit weird, but I have actually checked out “online” men without either of us getting out of our cars.

Make an Entrance

Back when I was dating, I liked to arrive a few minutes late when meeting a guy at Starbucks (or a similarly public place).

Why be a little late?

  • It gives you the advantage when making a first impression because you don’t seem desperate.
  • It makes you appear to have a busy, successful life, even if the most exciting thing in your life is Downton Abbey.
  • It is easier to stride into the room in a confident manner (head held high, tummy sucked in, scanning your audience) than it is to sit at a table all alone, staring at your watch, trying to keep up your nerve... waiting... waiting... waiting. Also, if the guy seems like a creep, you don’t even have to sit down.

I used to have a list of more reasons why you should always be a few minutes late and why your first meeting should be short and sweet, but I can't remember everything. The list was put together as a way to avoid a repeat of my worst experiences. No... nothing terrible happened to me. My bad experiences were more like, "What was I thinking when I said I'd meet this guy? He's so boring. He's so uncouth. He needs dental work."

Well, trust me. It’s just better not to be the first one there. If the guy leaves before you get there, he’s not that excited about meeting you.

Remember that most of the guys you meet online are not going to be your type. You can spot the excessively bad apples by reading between the lines of their bios, but oftentimes you won’t know which men are good and which men are bad until you meet them in real life.

If you think you like someone, and he meets most of your criteria, you’re going to have to meet him at some point. You might as well do it right.

Photo Credits: Main photo Flickr Creative Commons (Will have to look up name).

Safety Tips from Match.com

More Articles for Baby Boomer Women:

What Body Types do Men Prefer?

12 Places to Meet Men over Fifty in the Real World

Could You be a Targer for a Psycho?

Online Dating Sites: Cookie and Magnus

What do you think of this article? If you have any other ideas about meeting a guy for the first time, leave a comment at the bottom of this page. If you like this article, give us a Google Plus "thumbs up" with the "g+" button.

Tina Boomerina (AKA Christina Gregoire) is a Baby Boomer born at the end of 1952. Her mission is to make the internet a kinder and gentler place for Baby Boomer women around the world. Tina's specialty is fashion for women over 50.

Follow Me on Pinterest Follow My Boomer Lifestyle Blog on facebook

Related Posts


  1. Suzanne L'Hernault

    I was on Match.com for a year and a half before meeting my current boyfriend a year ago and I went on a lot of dates, sometimes 5 in a week. One practice I followed was to have a friend text me during the date to make sure everything was OK and to see if I needed a "rescue," i.e. an excuse to leave right away. If I needed an excuse, a phone call would ensue summoning me to some "emergency." Another practice I ALWAYS followed was to text upon arriving home whatever friend had been apprised of my date so she would know I had gotten home safely.

    The best advice I can give is to go with an open mind. You are not likely to meet the love of your life on a given date, but dating is the only way you are going to meet him. Consider each date as practice for the date where you finally meet "the one." Good luck.