In Which I Plan a Surprisingly Uncomfortable, Awkward Third Date

I’m great at planning dates.

“Toot, toot!” goes my own horn.

I have a blog that’s largely about New York events and dating! Of course I’m great at planning dates! Duh!

Now just because I’m great at it doesn’t mean I want to plan them all. Dude, if you are the one asking me out, you’re the one who should do the planning. That’s not even old-fashioned, that’s just logical. You don’t say “Let’s get dinner” to a chef and expecting her to cook it!

Dude was excited for our third date, he made that very clear. (You can read about the first date and second date if you haven’t already.) I was excited too. I hadn’t been on a day date in a long, long time and I love day dates. We were meeting at noon on Saturday and New York City was our oyster. The possibilities endless!

“We’ll do whatever you want,” he texted. Oh great, whatever I want. I rolled my eyes at the phone.

Fellas! Are you trying to impress a woman? Do you have hopes of ever getting in her pants? PLAN A FUCKING DATE! How is this not universal knowledge??

“Fine,” I thought, “You want me to plan the date? Then I’m gonna take advantage of you. Of you and your wheels.”

He’d mentioned on our second date that he had not one, not two, but three bicycles. Dude, that’s so cool. I used to bike every day as my main mode of transportation. (Remember? You can read the story of how my bike got its name here. SPOILER: it’s related to a 19 year-old South African I dated.) When I moved to a 5th floor walk up in Hamilton Heights I gave up my bicycle. I miss it…with an ache that becomes really intense on perfect sunny days…. This guy had 3 bikes just sitting in his apartment? He wanted to do whatever I wanted? Well, I wanted to get on one of those bikes STAT.

“Let’s go biking Saturday!”

And thus it was a plan.

Saturday at 12PM (no really, I was actually on time) I stood outside his apartment in Astoria. Stood there and realized how weird a 3rd date this was. Maybe I’m not so good at planning dates when blinded by bike lust! I was entering his apartment on a 3rd date with absolutely no intension of riding him…just his bicycle. Not a euphemism, his literal two-wheeled bicycle. I hope he didn’t have different ideas…

Despite failure to plan a 3rd date, dude was a total gentleman when I walked into his apartment. His nice, clean, studio apartment. (Duh, I was taking notes.) After a struggle to get down three flights of stairs carrying a bike (I declined his offer to help), we both stood outside his apartment. Again, I questioned my date planning skills. The bike was a racing bike, built for speed with a tiny little seat and handle bars parallel to the ground. I’d never ridden any thing like it. Holy hell was it uncomfortable.

I wasn’t wearing a helmet. I felt awkward on this bike that demanded I hunch over the handle bars. The seat offered no cushioning for my poor little ass. Ouch. I had planned an awkward and significantly uncomfortable date! But because I planned it I felt I couldn’t back out! Get your ass on that bicycle, Mary Lane!

So we set off down the non-existent bike lanes of Astoria. Him leading the way, completely at home on his bike, me following behind. Trying not to focus on the discomfort of my behind and the stupid racing bike seat no one bit made for lady bits.

How much was I going to regret this?

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About New York Cliche

NYC lifestyle blog by Mary Lane. Events, adventures, epic mistakes, dating, life, humor. A 20-something trying to make it (and make out) in the city of dreams.