Some Funnier Online Dating Moments

If you have been following me for a while, you will see that I have tried to give helpful online dating advice.  Although I know my sincerity sometimes gets misconstrued for humour, there are times when I can do nothing but laugh at the absurdity of some of the messages or interactions I have had. 

The Masseuse

A few weeks ago, I came across an attractive male’s online dating profile.  When I clicked on his picture to read his biography, as I do before messaging anyone, I was a little caught off guard.  Basically, he wrote that he was happily married and a friend of his told him about this dating site and how it could help his business.  The business was feet massages.  I was a little confused at this point as to why someone was selling something on a dating site for meeting people, but hey, fine.  Then the kicker.  He wrote that a friend of his had him massage her feet, and it was so wonderful that he needed to expand his business.  And that, perhaps once women found out how amazing his massage was, they would realize that they were seeking a foot rub, rather than a man.  Ahem, I am not sure a foot rub, no matter how amazing could replace a partner, but hey, maybe you do get what you pay for.

Here is another one for you, called Winning the Lottery

Although I joke about winning the lottery with E, I have never seriously considered even buying a ticket, let alone winning.  But a few months back I got a message that got me thinking.  I was approached online by a man who had actually won the lottery.  He was fairly old (mid 50’s), bought a baseball team and was dating a 23 year old.  To top it all off, they swing and were looking for a couple to date.  They travel around Alberta as they have the money to do so, to have hot nights with couples.  So many questions started running through my head.

Did this guy always believe in non monogamy or did winning 1 million dollars give him the confidence to do so.  Did the young lady know him prior to his winnings?  Does money actually make a man more attractive?   All these questions and more went spiralling through my head.  To bum out my readers, I never actually met the man in person.  I made my decision on this guy based on his profile and his picture.  I did not get swayed by the possibility this guy was telling the truth and would spoil E and I.  But it seems even millionaires use free online dating apps to meet people.  Who knew?

The Seduction, Well Sort of

Twice now, I have been messaged by cute blond girls.  Maybe it is the same girl, using a different alias each time, but either way, here is how this one goes.  “Hey Sweetie, you’re super cute”.  Me flattered of course engages in conversation.  Then after a few messages, the purpose is revealed.  “So, I have this fantasy, but each time I write in on this site I get blocked, can I have your number?”.  Me, being the paranoid lady that I am, refuse this request and ask for more information on what this fantasy is that could possibly get her blocked.   “I have this hot fantasy, where a stranger seduces my boyfriend, then I find out, and have really hot sex with him”.  Uh, what?  The game plan is, a woman finds another woman online, then organizes the two of us meeting at a bar, and then I have to do all this work to seduce the guy.  And the rub is, in both scenarios, the guy has no idea it is happening.  Basically I am making him cheat on his girlfriend, but in the end, surprise, he wasn’t really cheating because she orchestrated the whole thing!  So yay!   And well, no.

And as for the drawing, that was from a sweet moment, when I stranger online asked if he could draw me from one of my posted pictures. My own personal, Titanic moment, and of course I said, absolutely.  

So there are a few of my funnier, or crazier online dating moments.  As always, I would love to hear a few of your out there.  And I am sure, that there will be a part II of this post in the future!  Stay tuned…

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