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AGING IS A CHOICE Part 30 – Dating Over Fifty (Successful First Dates)


by Robert Manni

At any age, when it comes to online dating…until you meet face-to-face, nothing is going to happen. 

The texts, the phone call to qualify a connection, they’re all preliminary. Yes, they are important and necessary but the critical next step, going on an actual date, is what will make or break a potential relationship with a genuine person. 

When you meet, you’ll know rather quickly if things are going to work out. That is, if you’re paying attention. Don’t get hung up if you find the energy is different because it will keep changing from an online wink, an initial text, a phone call, or meeting a person out in the real world. Whatever happens, don’t take anything personally. Chemistry is random. Instead, focus on what you can control.

With that in mind here’s my game plan for making a first date a success and setting up a second encounter.

Adjust your expectations  

You’ve seen their photos, but you’ve never seen them in the flesh. I suggest considering the 85% rule across the board for looks and personality. That means, lower your expectations by 15%. Profiles are like ads. Everyone chooses their very best photos, and the pics are often dated. They will also paint a flattering description of themselves, too. So it’s important to reel in your expectations and hope for a nice surprise. Your potential partner will also be comparing you to your profile when you meet. It’s part of the game. 

Let your vibe be your guide

Don’t be too quick to reject someone new, but at the same time, trust your instincts. After a drink or two at the most, you’ll know if you want to see them again. It goes both ways. If it’s meant to be, you’ll both feel it. Chemistry is a feeling. It’s not an analytical process. Sometimes people will mistake what sounds good with what they actually feel about a person. Trust your feelings. Otherwise, the relationship will not feel authentic.

Actively listen, be honest, don’t reveal too much 

First dates are a feeling out process, so go with the flow and have fun. Without prying, find out what the other person is looking for as part of the conversation. They’ll share as they see fit. However, if you’re not getting straight answers, it may be a red flag. 

When you are asked questions, be mindful of what’s really being asked and give honest answers. Don’t be evasive. The truth eventually comes out, so be honest. If your answers are not what the other person hoped to hear, it’s okay. It’s better not to waste anybody’s time. 

Regardless of how comfortable the person makes you feel, be mindful not to dominate the conversation. There is an art to peeling back the layers about who you are that makes you more “mysterious” and attractive. Save some of your best personal stories for future encounters.

Keep it simple and make that first “date” brief

Do you want to take someone you have never met to dinner at a Michelin-rated restaurant? That’s up to you, but I suggest keeping the first date simple, and brief. Perhaps an hour to share a beverage somewhere nice, like an upscale bistro or coffee bar. That’s enough time to feel the connection without any pressure to extend the date if there is none. If the chemistry is strong, let that excitement and curiosity build for a second date.

What if it’s not happening? 

The heart wants what it wants. If the other person is not what you were expecting, even factoring in the 85% rule, it’s okay to cut bait in a courteous manner. Don’t fidget or look at your phone. Be curious and pleasant, finish your beverage, dispense with the check, and say goodbye with a smile. You never know if this person could become a friend or future business connection. They may even know a friend that’s perfect for you.

Taking the next step

If the conversation flowed freely, you both laughed and felt an attraction, and are interested in learning more about one another, congratulations! You may have hit the jackpot. Maybe you want to extend that first date by catching a bite to eat or walking a few blocks together. Whatever you decide, at the natural conclusion of the date, I suggest two courses of action. 

You can look them in the eyes and say something like, “I had a great time. Let’s do this again.” Then gauge their response. Or thank them for a great time and say good night. Then send a text a few hours later or call the next day to check in and set up a second date. Do whatever feels right, but don’t screw around and squander a connection that could turn into something lasting. 

I hope this has been useful, but of course, that’s all up to you. Remember, even when it comes to dating, it’s never too late, and you’re never too old because aging is a choice.