I don’t know where to start, there are not many things that went well; from him just standing there while I tried to find a Toonie to pay for my tea 
( I ended up putting it on visa while he had a $10 in his hand, talk about cheap date ) to having very little in common, we only went on one date which lasted about 1.5 hours but felt like 3!
His life revolves around his boys, they are, understandably, his world. However, he doesn’t have any other interests so there wasn’t much to talk about. He explained that he had recently moved to Toronto and had no social life, friends, etc., he complained repeatedly about how expensive things were (like going to a Jays game) and mentioned that he’s had the same job since high school. The fact that I was not attracted to him and found him socially awkward and completely uninteresting made conversation very difficult. I felt very frustrated after this date.
I met him via a dating app, I will not divulge which one, but needless to say, it was well known enough that I thought there would be some form of screening or vetting done. I can’t fathom how the app thought we would be a good match. I don’t want to sound like a snob, but I have to be honest; Michael is not someone that I ever would have gone on a date with had I talked to him, met him on my own, or through a friend, maybe that’s why I’m single….but I’m looking for something/someone extraordinary. Someone that has accomplished something! Someone that is attractive and that I’m proud of.
I’ve done a lot in my life and want someone that I can share experiences with. I started a business at 22 which is thriving, I’ve traveled to over thirty countries, was a world champion athlete and I now coach World Champion teams and have recently been cast as the lead in a television show. While I have many downsides (way too impatient for my own good!), I just want someone with life experience and that shows ambition, drive, work ethic, athleticism and charisma. Michael wasn’t that guy.
After I expressed my initial concerns to a friend prior to the date, I really went into it with an open mind. I had a conversation with him on the phone that was awkward, quite boring and cause for major concern at the time. I really tried to leave those feelings behind and see what could develop, but it didn’t take long to become very clear that he was not a good match.
Well, that sounded like a nightmare date, and we only have Caroline’s side of the story, but let’s break it down;
Are you financially secure enough to date? Gentlemen, if offering up $2 for a cup of tea is a financial hardship, you’re in no position to date. It’s not the Hope Diamond, it’s the absolute cheapest thing on the menu!
I’m sure your kids are awesome, and women do love a man who takes care of their kids, but your kids are not welcome on your date, especially the first one. The first date is nothing more than determining whether or not there’s any chemistry. Of course let her know you have kids, but resist the urge to tell her the scores of their last soccer games.
If you have no friends, make some friends before dating. No woman wants to feel responsible for your social life. Get a hobby, take up a suitable sport, and go from there.
Working at the same company for decades shows your stable and boring, contended and tired. It shows you’re a good provider, but does not mean you don’t have a good work ethic, Maintaining the same position without moving up the ladder could mean you lack ambition and that’s not attractive to someone who has drive and a passion for self improvement.
Girls, ask better questions. What does his dating profile say? If his kids are his whole world, I’m sure he mentions them in his profile. Look at the language that surrounds the subject of his kids.
What does his or her profile say about hobbies? Interests? Sports, Travel, or any personal flare. If there’s nothing there, you should not have any expectations to the contrary.
If you’ve spoken to him on the phone once already you’ve had all the opportunity you need to get more information. Before having a phone conversation, write down a few questions about things that matter most to you and question him or her directly on the matter before planning trips or experiences.
Physical attraction is hit or miss. Profile pictures can be deceptive, they’re only 2D and a mere moment frozen in time, if it’s even them, they can’t tell you he/she laughs like a hyena, slurps when they drink, or worse, so you best get as much information as possible before you go on any date!
