Writer. Advice giver. Peanut butter and chocolate enthusiast.

Advice for the Modern Man: The 3 Fundamentals of Dating


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(Question has been modified for space and clarity.)

I cannot get a date. While most will categorize me as old, I’m 66, and I’m an engineer with a challenging job. I still run 2 miles and bike up to 20 on a regular basis.

I’m on multiple dating sites and have sent out more than 200 messages, but have received very few responses. My sister and a close female friend have reviewed my profile, and I’ve changed it several times. 

The result has been four viable dates in over a year — one decided we could only be friends after a single date; two lost interest after a couple of dates (both lived nearly two hours away); and the last woman has another boyfriend.

I’d like to find a partner who enjoys ballroom dancing, who is fit enough to keep up with me on a reasonable run or bike ride, and who is educated. Is that too much to ask for?
–Alone in PC; Panama City, FL

Dating is difficult when you’re 16, and it doesn’t get any easier when you’re 66. The same challenges exist. Finding someone you connect with, someone you enjoy spending time with and someone who wants the same things out of life — that’s no small task.

Reading your struggles reminded me of my single days. When I wasn’t getting ignored by prospective dates, I was getting rejected by prospective girlfriends. Each dismissal was accompanied by an incremental decrease in self-esteem — and of hope that things would ever change. So I feel your pain.

My first inclination is to ramble about the fundamentals needed to survive being single. And because I believe there’s value in these principles — despite their eye-rolling cliched-ness — that’s what I’m going to do, at least for a minute…


1) You have to be active.

As Teddy Roosevelt said, the credit belongs to the man who is actually in the arena, whose face is posted in profile pictures; who strives valiantly for setups; who errs, who comes up short again and again on dates; who knows the great enthusiasms, the great devotions of asking for and getting that second “Yes”; who spends himself in the worthy cause of the first kiss; who at best knows in the end the triumph of the Walk of Shame, and who at worst, if he fails, at least he fails while daring to close the deal, so that his place shall never be with those cold and timid bachelors who know neither consummation nor cold shower.

OK, so I changed a lot of — and desecrated — one of the greatest speeches in American history, but you get the point. You have to be willing to try.

This is what gets you in the game.

2) You have to be persistent.

To be clear, not in the creepy, stalkerish, refuse-to-get-the-message kind of way.

But the more active you are, the more rejection/disappointment/embarrassment you’re subjected to. You’re investing time, money and hope, and in many cases, you’re investing all that in someone you’ve never met.

When things go wrong, it can feel as if they’ll never go right. That wears on a person. But it’s in those moments when you have to get off the mat and back into the arena.

This is what keeps you in the game.

3) You have to be (a little) crazy.

Jerry Seinfeld once declared 95 percent of the population undateable. And that was just based on looks. Factor in things like personality, values, morals, sense of humor and preferred bedtime thermostat setting, and that number has nowhere to go but down.

So it takes having at least one screw loose(ned) to believe you can overcome such hard data to meet the woman of your dreams.

This is what convinces you that you can win the game.


These fundamentals can help everyone, although they apparently haven’t helped you. (Yet.)

You’ve sent over 200 messages to potential dates (active); you’ve revamped your online profile multiple times, and you’ve given everything you had to every woman who gave you a chance (persistent); and despite all this leading you nowhere, you’re still not giving up (crazy…in a good way).

I admire your dedication, and for that, I want to leave you with some practical, actionable advice.

You mentioned your age as if it were a negative, but in this case, I don’t believe it is. Whereas younger singles don’t know what they want in a partner, you do. It says so in your submission. You want someone who is:

• Educated
• Physically fit
• Interested in ballroom dancing

Dating can be like a murder mystery — solving it gets easier when you know who you’re looking for. Short of a police sketch, you’ve got a decent composite. The trick is figuring out how to meet her.

So why not enroll in continuing education courses, join a running and/or bicycling club and sign up for ballroom dancing classes?

A few things to consider:

1) Few people value education more than those who go to school when they don’t have to. In your area, Gulf Coast State College and Florida State University Panama City offer lifelong-learning opportunities in business, personal enrichment and other subjects.

Spot an attractive woman in a course you like, and the two of you are guaranteed to have at least one common interest.

2) When I was a kid, my parents took ballroom dance classes at the local community center. I’d shoot baskets in the gym while they learned to cha-cha, but inevitably I’d end up watching the last few minutes of their class. It was amusing/terrifying to see the tension and toe-stubbing frustration among the couples who had disparate dancing abilities.

The lesson? Don’t commit to a romantic-dance partner until you’re sure you share compatible rhythm levels.

3) Need someone who can physically keep up with you? See above about ballroom dancing. Your biking and running outings should release stress, not induce it through constant stopping and waiting.

Plus, people can run or bike alone, so a certain portion of those in these clubs could be there to meet someone, as well. If nothing else, new friends could lead to new setups.

The most important aspect of these endeavors, though, is that not only do they put you in touch with like-minded people in a social setting, they put you in your element. When you’re where you want to be, doing what you want to do, you become the best version of yourself — which will make you that much more attractive to the best woman for you.


This article originally appeared on the Good Men Project.

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