Failing at the Dating Game

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I’m mid-way through my online dating challenge and I have learned a few things.

First of all, it turns out that my previous disaster on Plenty of Fish could have been my fault.

Apparently stating that you are looking to date but nothing serious is code for hooking up.

Although I still do not believe single girls use that site but whatever, I have now upgraded:

I am looking for a relationship.

I really think there needs to be a middle-ground of hey if I meet someone and settle down that would be great but I’m not desperate to get married because my ovaries are shriveling up.

Just a thought, I think it’s a nice middle ground. 

And with much encouragement from friends and strangers I am currently on OKCupid, Plenty of Fish, eHarmony, Match and Lavalife. Seriously are you happy people?

My friends are not.

Saturday night I met up with friends for drinks. B originally pushed me into online dating offering that a web site comparison would be interesting for readers.

He had been dating but frustrated that some girls would engage in conversation but then disappear.

So when I told him that I had spoken to a few people but then cancelled at the last minute because a nap was more appealing he was not happy.

He told me to get off online dating because guys like him were tired of girls like me.

But I protested no I really was up for the challenge.

I would make more of an effort. But there would be more scolding, my friend J asked me how it was going.

She was a pro with online dating and had done it for years before meeting her live-in boyfriend through friends.

J knew how it worked and wanted to know how many dates I had been on.

Two dates.

I thought that was pretty respectable but she called me out on it.

She pointed out that I could probably go out several times a week and I was not making an effort.

But it’s not all my fault I swear, just look at some of the messages I am getting.

And then there are the UR sexy messages or the guy who wanted to know whether I would rather go to the moon for 10 minutes or travel around the world for five years on 5K a month.

Oh and just yesterday someone who seemed normal mentioned he didn`t like a particular bar because there were too many coloured people so he just got drunk while there.

I am not the only one.

A friend at work who does quite a bit of online dating told me she once went out and her coworker recommended the milkshake with the chicken wrap and fries.

She thought things were going well until the food came and he took half of it on her plate saying oh no honey you can’t eat all that! 

She put money down on the table and walked out the door.

Abby from The Jungle Princess lives in Las Vegas, which appears to be an even bigger challenge.

While she states she has a day job so people don’t think she is a cocktail waitress she no longer says she is a creator after a former date Google-stalked her and knew her life story.

She has had many people lie about height, married status and one guy walked out on her during the middle of dinner because she made him realize that he was not ready for a relationship.

Sally from Unbrave Girl has the daunting task of dating in China.

Maybe I have it easy.

The two dates I had were totally normal. They were both nice guys, there was no spark but if I randomly see them sometime I’d be happy to say hi.

This is all to say perhaps I wasn`t giving this challenge the attention it deserved and I should take the remaining weeks to make a real effort.

Afterall, I just connected with someone a couple of days ago and I think they could be quite interesting.

Join the Conversation

  1. Betsy Talbot says:

    Ah! Such a great tease at the end! I once met a guy at a pizza joint who immediately told me I lied on my profile because I was taller than 5’6″ (I’m not, and neither was he).

    And another who told me he would do anything to find a woman as honorable-yet-sexy as his mother (check, please!)

    But the weirdest stuff was definitely online, and I’m convinced a lot of these people don’t have any intention of meeting someone face to face – for a variety of reasons.

    But there are some decent people – just like you! – who try these sites out. But like you, I think they give the sites a very short window to show value or move on. Probably a very smart move.

    Just keep in mind, these stories are GLORIOUS for your friends at happy hour and will prove to be entertaining for years to come. Enjoy the harvest.

    PS – And one for the guys: “Dude, did I ever tell you about this narcoleptic chick who would rather sleep than go out with me? What a freak!” 😉

    1. Ayngelina Author says:

      I know I know. Most people I know in Toronto have either great or horrible things to say about it but the one thing everyone agrees is that everyone is on it.

      I will give it a fair shot for at least a few weeks.

  2. Dating sites can be excellent for ramping up one’s social life. But the big events in life (like finding real love) happen whether one is actively seeking or not.

    1. Ayngelina Author says:

      Good point, I suppose I need a little ramping up 🙂

  3. I personally know how important those naps are for you!

    The response from Sexi Dominican was so off the wall. Who in their right mind would think read that and think..”There’s the guy for me!” LOL

    1. Ayngelina Author says:

      I asked another guy if anyone responded to “UR sexy” and he said “you’d be surprised”

  4. Stephanie - The Travel Chica says:

    If you need a nap, I think it’s best to take one rather than show up and be cranky.

    That’s my brilliant dating advice.

    1. Ayngelina Author says:

      And you know how much I need my naps!

  5. This is true, in my experience: “If you are looking for the love of your life, stop. They will be waiting for you when you start doing the things you love.”

    1. Aww Gregory, you romantic you!

  6. Renee King says:

    I’m scratching my head trying to figure out why someone hasn’t snatched up Sexi_Dominican yet? What a catch! I say that you should take your time and not hold yourself to a 30 day window. I think the best relationships happen when you aren’t looking for it. Now, that is not to say that you can’t find love online. I’m sure it’s possible and I think it’s a great way to eliminate the crazies a lot faster than usual.

  7. Not that you need any unsolicited advice, but I think I agree with Renee. 🙂 I have never done online dating but it seems like staying on until you meet someone you really strikes your interest is a good approach. My mom did e-harmony several years ago, and after a few months of “getting to know” some guys on there, she and one guy finally met in person, and now they’re married.

    1. Ayngelina Author says:

      Wow that’s impressed, I should get my mother on it…

  8. I’m so proud of you for sticking with it! I believe in the system — I met my last boyfriend on-line. I have two dates this week. Someday one will stick!

    1. Ayngelina Author says:

      Okay I have two this week as well. Fingers crossed I don’t need a nap.

  9. Ack!

    Dude, I feel for you. Before I learned to meet women in real life, all I did was online dating.

    Unfortunately, the webs are filled with freaks that appear to be some brand of messed up robot sent from a distant galaxy to test my sanity.

    No joke. The one that was 80lbs heavier than her profile pic. The one that showed up and told me her nickname was “Evil”. The one whose hobbies included “nothing” and “msn”. The one that never showed up because “I was busy”, but then constantly texted and called me because “I’m bored and lonely.”

    As such, I am now convinced that online dating is the devil.

    Ayngelina, Toronto has a thriving social scene. Just get out there and meet real humans! If I’m ever in the area again, I’ll take you out and introduce you to many a cool dude.

    1. Ayngelina Author says:

      Haha perhaps it has changed a bit since you last did it. I think there are a lot of freaks online and offline. So far no love connection but I have met nice people.

      For the record I did not meet Sexy Dominican.

  10. Kent @ No Vacation Required says:

    I vote for finding someone on Maui! How does that sound?

    1. Ayngelina Author says:

      Kent as always you have the wisest advice!

  11. Dating is like warfare. Good luck! Russell

    1. Ayngelina Author says:

      warfare? how?

  12. Have you tried my technique of standing really close to the guy at the checkout counter until he buys you dinner? That seemed to work really well for me… and by “well” I mean “the guy actually talked to me for a bit.” I’m pretty sure that means we’re getting married.

    1. Ayngelina Author says:

      Yeah I so hate to complain, you either have to ask out every foreigner you see or learn Mandarin well enough to date a local.

  13. Natalie T. says:

    “or the guy who wanted to know whether I would rather go to the moon for 10 minutes or travel around the world for five years on 5K a month” The funny thing is I got the same message from the SAME guy. Sigh.

    The last date I had I went to the wrong restaurant and told my date while I was on my way to order the guacamole. He ate the guacamole.

    And that is why dating in Toronto is so hard.


    1. Ayngelina Author says:

      Yes we seem to attract the same people yet don’t have the same taste, rather odd.

      Although we both agree the travel question doesn’t work on anyone.

  14. Leah Travels says:

    My best friend was on eHarmony before finding her husband through Match. One particularly bad date she had invited her to a baseball exhibit at a museum. Not bad. Except when she met him in front of the museum, he was dressed in a baseball uniform! I can’t make this stuff up.

    1. Ayngelina Author says:

      Did she take a photo? I would try to take a photo!

      And then probably share it all with you.

  15. Valerie Hamer says:

    I have had my share of creepy blind dates. One guy was much shorter than he said, though what stood out more was his constant talk about his mother.

    Then there was the guy who claimed to be ‘above average’ in looks, he sent a picture that was truly scary. (Think serial killer.)

    1. Ayngelina Author says:

      I won’t talk to anyone who doesn’t post photos. Not because I need to know what they look like but I think it’s tough to post a profile and photos and if I have to do it so do they.

      I do tell the guys that, and I did tell the weird moon question guy that it was a weird ice breaker.

  16. Jade - says:

    keep at it! Im sure you will meet someone at least not too creepy eventually

    1. Ayngelina Author says:

      The two people I met were nice. So at least I know how to weed out the weird ones. There was no love connection but if I ran into them again I’d want to talk to them because they were nice, and most importantly, normal.

  17. Hahaha, some people really lack in social skills!

    1. Ayngelina Author says:

      No joking I just got this gem: Hi, you seem overweight to me in pictures, are you fat?

  18. I met my current boyfriend on I had to get over the fact that his spelling is atrocious but he’s the most wonderful person I’ve ever met.

    1. Ayngelina Author says:

      I don`t know if I could get over spelling, it`s actually a big issue for me. But perhaps I need to learn that those things aren`t dealbreakers.

  19. I actually had a guy grab my foot under the table on a first date once. Ah, internet dating. The memories.

    Also, fun fact: online dating is now the #2 way couples meet. #1 is being introduced by friends. It’s very, very common. And apparently it works!

    1. Ayngelina Author says:

      I’m not surprised at all. It`s pretty difficult to meet someone out at a bar so unless friends introduce you the only way is online.

  20. Micamyx|Senyorita says:

    Keep us posted! 😀

  21. Many of my girlfriends have atrocious online dating stories, you are most definitely not alone. I hope it works out!

    1. Ayngelina Author says:

      It`s actually one of the upsides to online dating, sharing the funny stories with people.

  22. I always believed that people meeting on the Internet are looking only for sex. But that may not be the case as i see…

    1. Ayngelina Author says:


  23. Great hook at the end Ayngelina. It’s starting to feel like watching a romantic comedy film. Now I want to know how it ends 😉

    1. Ayngelina Author says:

      Does this mean you are promising me a happy ending?

  24. I’ve never done online dating, but I agree with you- they need another category of “I’m not just desperate to get married, but I’d get into a relationship if I found the right guy”. Can’t wait to hear more 🙂

    1. Ayngelina Author says:

      I know, right??

  25. bahaha that message is horrible/awesome. It makes me miss Myspace, because that is basically what my inbox looked like. I think all of you are brave for trying. Honestly, I have always hated dating but always got fairly “lucky” and ended up dating friends, thus skipping the whole awkward dating phase. Of course, dating in Argentina was a big slap in the face, perhaps payback. Keep trying and maybe nap just a LITTLE less.

    1. Ayngelina Author says:

      True you put up with worse for much longer in Argentina, that is why I can never live there!

  26. Bret @ Green Global Travel says:

    Online dating (which I did off and on for YEARS after my divorce in 2004) is like any other social venture: You can’t win if you don’t play.

    I think the mistake a lot of online daters (myself included) make is that they do it with specific goals in mind, forgetting that it’s mostly about making connections.

    The second girl I ever met through online dating (through Lavalife, just FYI) ultimately became a good friend, and it was she who introduced me to Mary 4 years later. We’ve been together 3.5 years now…

    1. Ayngelina Author says:

      Bret that`s really encouraging. Actually I have tried to take the perspective that even if it doesn`t work out as a love match I meet interesting people – at least the last two have been.

  27. I can’t believe you turned down sexi_dominican….he seems like a real catch 😉

    I think it’s awesome that you’re putting yourself out there & trying online dating. You’re braver than I am! (Although I kind of want to try it just so I can get ridiculous messages from real class acts like “his sexiness” the Dominican)

    A lot of my friends (in real life & blogosphere) have similar stories as you do when it comes to the process of online dating. From what they’ve told me, a lot of it is a numbers game (increasing your chances by trying to meet as many people as possible) and a lot of it (like real life) is just luck/fate/destiny what have you.

  28. I think some of the best blogs I’ve read have been about online dating but they’ve also kind of scared me off them too. It doesn’t sound as though you’re being fickle, though, hun. It sounds like with some of the quality of the messages you’re getting, a nap is definitely the better option.

  29. Austin-Lehman Adventures says:

    Hang in there. Maybe it is better that your just find some nice guys to be friends with while your traveling. Better to find Prince Charming once you know where you want to stay forever right. And at least your meeting decent guys, albeit not the right guys but nice guys to have a good time with. Good luck to you.

  30. I think the two of us could have a pretty interesting chat about online dating… I’ve decided that the main reason I do it is for the amusement of my friends. Most recent message I got as an opener:

    “Hey, are you a good driver? Me and my best friend, are robbing the bank across the street, and guess what. Driver screwed us. All you need to do is pick us up at 2:32 am, and drive to the airport. You get 3%”

    You want to think this is just a funny joke, but given the people I’ve encountered on the site, I’m really not sure anymore…

    1. Ayngelina Author says:

      Oh wow that is really weird. I think some guys try to be too clever, I would never write something I would not say.

      Although maybe he would say that.

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