
Most of what you read about mature dating tells you it’s a negative experience . . . especially your first date.
Dating sites warn of all the mistakes people make and all the bad things that can happen.
Cosmo and I are as guilty as anyone. We write a lot about the negative aspects of dating, for both men and women over 60.
Our intentions are good. We’re trying to help others navigate the often rocky road of mature dating, and learn from the many mistakes we made.
But it’s good to look at the lighter side . . . at least once in a while.
So for a change, let’s have a little fun with dating, and keep the mood upbeat, as I tried always to do when I was in dating mode.
I had a mantra rolling around in my head, as I got ready to go on the many first dates I made it through:
- Go into it with a positive attitude.
- Relax and enjoy getting to know another human being a little bit.
- Smile and laugh as often as possible.
- If things don’t work out, it’s okay. There will be other dates.
A sense of humor is an attractive trait to most of us.
Many of us put a sense of humor high on our lists of must-haves in a life partner.
But what’s funny to one person isn’t universally funny to the rest of the world.
On a first date, I liked to gauge my date’s humor IQ by testing it . . . if I thought they had potential as a partner.
When I felt especially good about the man, I had a little trick I used. I’d send him this message the day before, or early the day of the first date, to help him easily identify me:
“I’ll be the one in the lime green tube top and gold lame micro mini-skirt. How will I know you?”
Their reactions said so much . . . first, when they responded to my message and then when we met, and some of them expected me to actually appear in that get-up. Whether or not they thought I’d actually wear a micro mini-skirt, my little ploy loosened things up.
In a Psychology Today article, evolutionary psychologist Gil Greengross Ph.D., noted:
“Humor is one of the clearest markers of a successful social interaction. You can use it as an ice breaker, and sharing a laugh with others is a good sign that you’ve hit it off. Humor might be even more important in dating, where it reveals something about you or your potential partner’s intelligence, and also signals mate quality.”
Try to demonstrate your sense of humor in your online dating profile.

In my dating days, I spent a lot of time writing my online dating profiles, and tweaking them. I wanted to differentiate myself and give some feel for what kind of person I am.
Instead of just saying “I have a good sense of humor” or “I love a guy with a good sense of humor”, I did my best to indicate what kinds of things tickled me, by giving examples.
The men I dated often told me they became interested in me because of the nuggets I included in my profiles.
In an eharmony article, research scientist Jonathan Beber cited a study that evaluated dating profiles and found that:
“Men were more likely to describe themselves as funny, whereas women were more frequently found to say they were looking for someone with a great sense of humor. In the final portion of their study, the researchers inserted a funny ‘one-liner’ joke in a fake online dating profile to see how it would affect the desirability of this potential date. The result? Including a joke would make men more romantically interesting to women, but did not make women more romantically interesting to men.”
Despite the above findings, I still advise women to show the humorous side of their personality in their online dating profiles.
In the spirit of keeping first dates easy, breezy and light . . .
Given how stressful dating can be, it can only help to keep your mood upbeat while you’re navigating first dates.
I’ve put together a few things here that I hope will give you a chuckle.
Another eharmony article outlined 15 reasons a sense of humor makes you hot, including:
It’s one of the best flirting strategies. As actress Nia Vardalos said,
“Compliment a woman and, sure, she will smile. But make a woman laugh, and she may get naked.”
It points to having an agreeable personality. A big part of what it means to be personable is the ability to joke and share funny moments with others.
It assures your date that you are a happy person. Having a lighthearted approach to life makes for happy individuals — and of course happy individuals make happy romantic couples.
Add pizzazz to a first date with some humor.
Pay attention to the vibe between you two on the first date.
If she or he is making good eye contact and seems to be engaged in your conversation, she/he is at least somewhat interested.
If it feels comfortable to you, try interjecting something lighthearted, like a joke or something funny you read.
A post on Thought Catalog listed several funny tweets on dating by various people. (Even if you don’t use these on a date, I think they’ll help lighten your dating experience.):
Spice things up in a first date by wearing a parachute and refusing to talk about it.
The dating process is basically just guys pretending that they like to leave their house.”
“Nothing like filling out a dating profile to make you realize how boring you are.”
“Saw a couple holding hands while jogging and it made me hopeful that one day I will meet someone who will hate them with me.”
More dating laughs (I hope), and things you might share on first dates.
Cosmo and I recently re-watched the Frasier show on one of the streaming networks. If you haven’t seen it in a while, give it a go. It’s a great way to get your mind off the negativity of dating and onto some truly funny material.
Over the 11 seasons and some 260 shows, there was barely a clunker in the lot, but we both picked the episode below as our favorite, for the performance of Niles’ (Frasier’s brother), as he’s preparing for a first date, that happened to be on Valentine’s Day. (Stick with it, the clip takes a minute or so to really get going.)
Even the New York Times crossword puzzle jumps onto the dating bandwagon.
Coincidentally, as I was writing this article, I was working on a Sunday NY Times crossword. Entitled “Love at First Site”, the big clues revolved around clever names for dating sites. Here are the clues and answers:
Good name for a deep kissers’ dating site? French Connection
Good name for a dating site full of hot dudes? Stud Finder
Good name for a dating site of massage therapists? Rubber Match
Good name for an extreme sports dating site? Action Items
Good name for a non-monogamist dating site? Open Flames
Good name for a dating site for lovers of natural foods? Organic Chemistry
Good name for a “High Noon”-themed dating site? Western Union
Good name for a carpentry dating site? Board Meeting
For more fun dating stuff, see Cosmo’s post, 5 Funny Worst Date Stories from the Boomers’ Favorite Sitcom Characters.
More on Mature Dating First Dates
5 Things Men Should Never Do on a First Date
What Mature Women Lie About on First Dates and How You Can Quickly See It
How to Turn First Dates into Second and Third Dates – 4 More Tips for Dating Over 60
5 Smart First Date Tips for Singles Over 60
Dating Someone Who Drinks When You Don’t – 5 Tips from a First Date Gone Wrong
Humor works great if you are somewhat funny. If not can lead to silence from your date. I know my jokes are funny because my dogs are always laughing at them.
Thanks Jerry for the comment. Yes, humor can be a two-edged sword, especially if you use it in a way that’s not aligned with your personality.