lang="en-US" prefix="og:" class="no-js no-svg"> The Good, The Bad, and The Funny! On and Off-line Dating Over 40 - Antthemes

The Good, The Bad, and The Funny! On and Off-line Dating Over 40

A brief and hopefully, funny, overview of the dating over 40 experience, once you’re off that on-line dating site and actually out on a date!

This is what to expect once you are tired watching videos at yespornplease and get offline and out in the real world!

Forever Cyberpals

At some point, if you’re actually looking for a relationship, you’ll have to get off that Internet dating site (or sites). Beware of the person who’s happy to linger in cyberland indefinitely. This phenomenon has been discussed in various mediums, including talk radio where a psychologist linked the increased odds of a relationship failing with too much time spent in constant emailing.

I can corroborate that with one of my early online dating experiences. I emailed and talked on the phone exclusively with a man who lived quite a distance from me. When we finally did get together it was wonderful, even magical, and probably doomed from the start! My expectations, if not his, were totally out of sync based on the sense of closeness our months of “revealing” had created.

Digging Deeper Than the Profile

We all want to put our best self forward in our online profiles, especially those of us who are in the over-40 crowd. And with age should come a little wisdom, right? But behavioral economist, Dan Ariely, in Chapter 8 of his book, The Upside of Irrationality, cautions that dating sites “skew our perceptions.” Put in layman’s terms, you need to look past the prose to what the writer is really saying – or isn’t.

If someone doesn’t mention their family, for instance, that’s a big red flag for me, as a family is a vital component of what I’m looking for in a partner. Ditto, for someone who spends the bulk of their profile discussing their career aspirations, six-figure income, and desire to meet a like-minded individual.

Translation: I got fleeced in my divorce and am not going down that path again. While that’s a reasonable thing to discuss at some point down the road, it reeks of having not moved on from the post-divorce stage of denial, anger, acceptance. And speaking of moving on…

Jumping Right in the Pool

There are definitely two sides to this approach. While you don’t want to be permanent cyberpals as you see on the websites like bedpage, I am wary of the person who wants to meet or exchange phone numbers before you’ve even responded to his email. And most reputable dating sites concur with this opinion, warning their clients not to reveal too much personal information too soon or meet in a non-public place.

I have personally broken this rule. On the other hand, I had communicated with this person for almost four months, had worked with him on a business project, and knew key personal information. While everything turned out fine, I don’t recommend it. And though it sounds like a no-brainer, use common sense: meet in a public place, tell someone who will be reachable where and when you’re meeting the person, and follow up with that person afterward. And speaking of meeting…


This is it: the Big Reveal. Whether you’ve been emailing, texting, or phoning for days, weeks, or hopefully not – months – you are finally meeting this person – well, in person! Some well-learned advice:

  • Be Realistic. This is not the time for “Great Expectations.” I had a friend, a widow, who went on a first date and met the man at a nice, upscale restaurant. Things had not even moved past the appetizer when he pulled a small square box out of his suit jacket to reveal…..yup, you guessed it. The first date was the last date. Enough said.
  • Just Breathe. While a few butterflies or that queasy feeling in your stomach is probably a good thing, if you seriously feel any sense of alarm, just leave! Trust your gut; it has probably served you well up to now. On the other hand, if you just feel the person isn’t for you, see the date through; that’s just polite! Don’t do what one person did to me. He picked me up at my house (not a good idea, by the way), drove around for an hour talking mostly about himself, and then deposited me back at my doorstep!
  • Verify, but Don’t Go Overboard. Most online sites have a Verify ID (for an additional fee of course), to verify information about the individual you’re thinking of dating. Don’t become paranoid, however, and turn the first date into an audit. A friend, who is also in the “Over-40” Internet dating pool, actually had a woman he met online request that he bring his tax records with him on the dinner date so she could verify his income!
  • Don’t Discuss The Ex. If all you can think of to talk about on a first date is your ex, then you’re not ready to be dating anyway, internet or otherwise. The same goes for your dating partner. I have, as have countless of my friends, endured endless conversations on first dates revolving around the person or persons that have done the individual wrong. At some point, you start to think they probably had some good reasons!
  • Better Luck Next Time! OK, so you followed all my well-learned suggestions, others’ advice, and your own and the date was A) A disaster; B) A big snooze C) Great from the other person’s viewpoint but for you – not so much! Remember, that one date does not define your dating future. Pick up what tidbits you can from what went wrong or right, what your own expectations (and the other persons were) and move on.

Or as my late father used to say to me, “After all, even the worst date guarantees you a free hamburger and french fries!” He, of course, was from the generation where men always paid and cholesterol wasn’t worth thinking about. But I agree with the sentiment!

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