Today we debrief with Sasha, a 25-year-old Brookline resident and the co-coordinator of the Ministry of Fun at the Moishe Kavod House.

created at: 2013-10-08So I have recently been doing this online dating thing. It’s not my favorite, but it seems to be the way that many people meet these days. I always find it fascinating how people connect online. We both like hiking?! Traveling?! We have the same favorite coffee shop? Hooray! So I was pleasantly surprised when I found someone from my mid-western hometown who rated my profile highly. I felt like it could be a great conversation starter. We exchanged messages online for a bit. When I was home visiting my parents, he even recommended a local bar. We quickly made plans to meet up when I returned from my trip. I learned that he was in town visiting his younger brother who had just moved to Boston. He was hoping to find a job in Boston too but just hadn’t found one and moved here quite yet. It was less convenient, but not a deal-breaker for me.

Once we got to planning, though, things started to go downhill. He wanted to go to Uno Chicago Grill because it reminded him of the Midwest. Really, Uno’s? It’s fine, good deep dish, but for a first date? He was staying in the Brookline/Brighton area and was only in town for a weekend, so I suggested a few more unique local pizza options, such as OTTO Pizza or Jimmy’s Bar & Oven. Apparently that wasn’t his thing; he insisted on Uno’s.

Once we were there, it was fine, I guess. We had mediocre, one-sided conversation while he gave lousy eye contact. I did have a decent pizza, yet was even more confused when he didn’t get deep dish (isn’t that the whole point of Uno’s?).

By the end of the meal, I was quite ready to go home. As we walked toward the T, I casually asked where in Brookline his brother lives. He said Washington Square. Me too! What street? Then he names my street. I apprehensively asked him the question that I knew was going to make my stomach curl: “What apartment?” Yep. Same. Building. He was staying in the apartment two floors directly below me. How was that even possible? We met online!

So then we hop on the T and head to my (our?) street. We walk up to the apartment and what do we find but his brother and his mom putting together IKEA furniture. Classic. Everyone had just moved in and his brother’s two roommates were excited to meet me to ask me about the laundry, trash and recycling in the building. His mom was excited to play Jewish geography. I meet the mother on a first date? And on a bad first date, at that. A bad Internet first date to top it off! After about 15-20 minutes of awkwardness, I politely said goodbye and headed up the stairs to my own apartment to go to sleep and try to forget the weirdness of the night.

I woke up to a text message the next morning: “Want to do lunch?” I quickly rejected, and I actually did have other plans. But first, I needed to do my laundry.

And, of course, walking to the basement, wearing my lovely Saturday-morning sweatpants, I ran into the whole gang again. Just what I wanted. Not.

His brother still lives there; I still live here. I have a feeling the awkward isn’t over. Oy.

What’s your worst date story? Funniest? Most awkward? Lessons learned? Let’s debrief. Send a few lines or a few paragraphs, whatever your style, to