Datebook

20-something singletons from a Toronto-based ad agency airing dating dirty laundry for your mindless entertainment.

Part I: Irish Patios, Dock Adventures (& lack of blogging as a result)

This week was the week of extraordinary gentlemen. It was also the week of extraordinary busyness.

Having strategically secured a couple of top priorities for dates (The Jock, a 30-something marketing professional & self-proclaimed patio whore, as well as The Bachelor) I was able to sit back and let things fall into place.

Wednesday night The Jock called which scored points on many levels: 1) We haven’t particularly talked that much on the site, so this guy clearly has balls, 2) The phone conversation was actually fluid (sans white noise) and 3) His initiative didn’t stop at the call… he proceeded to offer up plans for Friday. Impressive.

Thursday we talk concrete plans and he suggests driving range at the docks. This is a great date suggestion as golfing is something I’m horrible at. My backswing is about as sexy as my lap-dances, so if he finds me attractive after this, it’s a big step.

In the meantime, The Bachelor also comes up big on Thursday. He calls after work and suggests we meet up for drinks. Up until this point, this guy has been a complete mystery. He seems interested and we talk intermittently, but things have been moving slooooowwwwly. This isn’t a huge problem but at the same time, if we meet and are repulsed, serious time and effort has been wasted.

Most awkward entrance of life: He’s already sitting on the patio and I have to go into the restaurant perplexed and say I’m looking for somebody. This is fun because the girls now know I’m an online dating mutant. I proceed to do the walk of shame outside to him. The Bachelor is strapping and as I get up to hug him I’m overjoyed that even 4 inch heels would be appropriate (walking in these heels would be a different story).

TB is incredibly adventurous: He cooks, he explores and above all, is incredibly intelligent. We go back and forth with questions and all the while I kick myself for previous evaluations and assumptions I had made.  There is something incredibly intriguing about somebody who can teach you and expose you to things you’ve never encountered. Whether The Bachelor is the guy to do this or not, I know this is a direction I’d like to go in.

Perhaps my absolute favourite thing about TB is the fact he grew up surrounded by women. He didn’t jump off a cliff through these experiences and additionally came out with a greater appreciation for the female population. It is quite obvious that he is caring and genuine and I look forward to perhaps meeting again.

As for red flags, he’s a Scorpio. What are the chances?