Guy's Guy™

5 Surefire Ways To Have A Successful First “Meeting” With An Online Connection


Image courtesy of Courtney Carmody

After you’ve shared a phone call that elevated your new connection to the oral word, it’s time to meet her. This can be the start of something big, or not. You’ll probably know fairly quickly and the odds of it working out are well below fifty percent.  That’s not to say that there’s something wrong with either of you. It’s just that if life were that simple, the online ladies in waiting would all have their very own Prince Charming that looks like Clooney and the guys would have a Playboy playmate with a PHD who loves watching football and can cook southwestern food like Rick Bayless.  Here’s a basic game plan for making that first date count.

1- Adjust your expectations.  

You’ve never seen her in the flesh, so you have no idea if that first look will exhilarating or a letdown. Face it. If you don’t connect with her looks, it’s not going to work out for long. No judging. That’s just how we homo sapiens are wired. I suggest discounting your expectations from what you’ve seen in her photos by 15%. That gives you an opportunity to be delighted and sets your reality barometer at the proper level. Everyone chooses their very best profile photos and some pics are going to be dated, so get over it and hope for the best. She’ll be doing the same thing when she eyeballs you for the first time.

2- Let your vibe be your guide.

Dinner at Daniel? Be my guest, but I suggest allocating an hour for a glass of wine at a reasonably nice establishment or even the old standby, Starbucks, if you’re not quite sure what to make of her and she doesn’t drink alcohol. If she doesn’t drink and you feel a connection, take the high road and meet her at that nice wine bar and spring for a cranberry and club soda. If you follow my previous tips and have gotten this far, it’s a good bet that this could be a real connection for you. Just keep the first “date” simple.

3- Actively listen, be honest, but don’t reveal too much. 

Even if you both are digging what you see and have an easy, free-flowing conversation sprinkled with laughter, make sure you allow her to tell you what she wants and don’t pry for more. Then, when she asks you a few things, consider what she is really asking and give her an honest answer. If she doesn’t ask you anything, it’s probably a one-time meet up. That’s okay─ you don’t want to waste your collective time if she is not feeling it. Respect a woman’s prerogative.

Don’t be evasive if she asks your age or if you’ve been married. Fess up and get it over with. She wants to know and she’ll eventually find out.  And if she doesn’t like the answer, it’s curtains anyway. And regardless of how much fun you’re having hold back some personal info, like your being a Reiki Master, for another date. She’ll appreciate peeling the layers back to reveal the mysterious man that you are.

4- If it feels right, order some food or suggest someplace different for a casual bite.

That’s it. Keep it simple and keep it to an hour or so. If it’s meant to be, you’ll see her again. And if you think meeting for a drink or coffee is boring, be my guest and enjoy your scuba diving lessons or ice skating.

5- What if it’s not happening? 

The heart wants what the heart wants, but be gentlemen. If she is not as advertised or just very sweet, but not your type, she is still a person with feelings and a woman deserving of your respect. Don’t look at you watch or play with your phone. She might be a really cool person and someone that could become a friend. Yes, a friend. But leave that up to her. When the bill comes, take care of it─ you asked her out─and then offer to hail a cab for her. And even if she’s not a keeper, remember to say good night with a smile.

Think you’re ready to take the situation offline?