Like many women today, I found myself unexpectedly single, over the age of 40, and forced out into a dating world that had dramatically changed in the 15 plus years since I had last dated. I had two choices: I could either play like Rapunzel, stay in my tower, and hope that my prince would come find me (which I knew would never happen) OR I could take the plunge, force myself out there, and at least make new friends, even if I never found my prince. I chose option two.

One thing I have never been accused of is doing things half-assed. If I am going to do something, I am all in, so this was my approach to dating. I figured it was a numbers game. The more I put myself out there, the more likely it would be that I would find my prince. So, boy did I put myself out there.

Very reluctantly, I tried online dating as I was told that in the new millennium this is apparently where the princes hang out. My full throttle approach meant that I needed to put a profile up on many sites, free, paid, well known and lesser known. What I learned was that online dating was like a beast I had never encountered before. Yes, there are good people on dating sites. Yes, it is possible to meet your prince. However, it is a complete minefield for the deer in the headlights that I was when I first dipped my toe in. Here are some of the lessons I learned:

  1. The same people are on all the main sites.

This means that there is no point in using a paid site because you will find the same people on the free sites, and I didn’t find the paid sites any more effective at weeding people out.

  1. Online dating has an etiquette all to itself.

I am girl who was raised with manners. When people speak to me, I respond back. Well, in online dating this is a problem. If someone sends you a message and you view his profile and determine that you aren’t interested, DO NOT, and I repeat, DO NOT respond back. I know this seems incredibly rude, but I learned the hard way that if you respond, he thinks you are interested, and at some point you are going to have to tell him that you aren’t, and then he will get upset and be rude to you. The way to avoid this is not to respond, as rude as it seems.

  1. Lots of people do lie in their photos or profiles, but in my experience most do not.

Yes, I met a few guys who were older than they looked in their photos, or shorter, or heavier, but for the most part, I have not found that most of the men I met lied. I have heard many horror stories on this issue though so maybe I have just been lucky.

  1. Apparently meeting someone for the first time is NOT a date.

I’m old-school. If I am meeting a guy who I am interested in for a coffee, a drink, or a meal, I put great effort into looking my best, dressing nicely, and showing up in a positive mindset. I do this because I consider this to be a date. I have learned that it is not. So ladies, when you are getting all dolled up to travel across town to meet your prince at a coffee shop miles from your home, remember this is NOT A DATE.

  1. The rules have really changed about who pays for a date and it has become extremely complicated.

Again, I have to repeat, I am old-school.   This means that the person who invited the other person out should pick up the tab. Seems simple to me. However, who should pay has become way too complicated. Some people are offended if the man doesn’t pay, some are offended if he insists on paying. There is really no easy way to navigate this issue other than to keep an open mind and not read too much into what happens. I still think the person who asked the other person out should pay, so I stick with that. You may have a different opinion and that is fine too.

  1. Like anywhere, you will find that there are crazy and normal people.

Despite the crazy people, the weird people, and the rude people, there are still some very nice, attractive, normal people who have resorted to online dating as a way to meet men and women. For this reason, I do believe that anyone over 40 who is seriously interested in meeting someone, should use online dating as one of their tools.

I have tried to summarize the key points from my online dating experience. I could write a novel on this topic. Hey, there’s an idea. If you would like some coaching on venturing back into the dating world after many years in a relationship, please contact me, as I would love to work with you.



Leanne Townsend
B.A., B.Ed., LL.B.
Life Coach

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