My Week on Tinder
My Tinder Bender Date 23.5 - Boston Part 2.


It takes me exactly ten guesses to figure out he’s a Gemini. As knowledgeable as I am with astrology, Gemini’s are a curve ball. One second, they’re spontaneous and carefree, and the next, they’re saying something so intelligent you can’t help but say, “Hmmm…. I never thought of that…” How am I to know whether he’s Air/Fire/Earth or Water? Too tricky.

I enjoy each and every wrong guess. He probably thinks I’m guessing wrong on purpose, to score extra smooches, but I really did feel some Pisces vibes. We continue bonding about random shit, like pennies. I tell him we don’t have pennies in Canada anymore, we have a cash rounding system.

“Oh! That explains it. I thought the Tim Hortons lady was just being lazy last time I was there.”

My paranoia about him being a murderer, and me being a hooker, is flying out the window. (Though if we were both those things, we’d actually make a pretty hot couple.) The interview style questions of a first date go back and forth, some serious, and some sexual.

Him: “What’s your favourite position?”

Me: “Starfish.”

(Don’t wanna brag, but that line killed.)

Every time one of us goes to the bathroom, we enjoy some fun roofy material.

Him: Don’t roofy my drink.

Me: I won’t. I couldn’t get them across the border.

The night is still young, and since we’re both tourists here, I can’t help but suggest something touristy.

“Let’s go to Cheers!”

Obviously I grew up watching and LOVING that show. How can I not make the most of the night in Boston, without checking out Cheers? (Do I have to put Cheers in italics if I’m talking about the bar, and not the TV show? Probably not, but I like the way it looks in italics, so I’m leaving it.) I also briefly babble about how I preferred the Rebecca years, versus the Diane years.

I pay for the cab there (obvi.) We arrive, and there’s a bunch of drunk business men, outside smoking. They are more than eager to assist with my Instagram photo shoot. (This man obviously thought I said, “Can you take a picture with us?” instead of “Can you take a picture OF us.” Oh, and that’s my date on the right. I didn’t blur out the business dude, since he really wanted to be in the picture.)


Inside the bar, our new businessman friend wants to buy us a round. He snaps at the bartender who is NOT impressed by him. She snaps back at him,

“I ain’t serving ya no more.”

We found Carla! Although, she seriously wouldn’t serve him, and somehow she thinks we’re with him, and we suffer the consequences. We continue bumbling through Boston. I decide to text my Airbnb roommate, and let her know I’m enjoying my date. I still kind of want to hang with her though. She seems cool. Why can’t I score and make a friend on this trip, right?

We head over to The Franklin on Dorchester, which is her local. I introduce the two of them (Oh God- I hope they don’t think I’m pursuing a threesome…) I decide it’s time for a snack again. You should always keep eating when you’re drinking, so you don’t get too drunk. (One time I was at Origin, and couldn’t afford the food on the menu, so I went to the bathroom and quickly ate a Cliff bar. I always keep those things in my purse as emergency damage control food.) I ordered what I thought was a cheese plate, but was actually a deluxe grilled cheese sandwich. I’ve never been so thrilled. (And inspired. I’m going to start to put grapes in my grilled cheese sandwiches from now on. Don’t judge me.)

My roommate is recently single. She just got out of a SEVEN YEAR relationship. Holy Fack! Like I’ve ever been in one of those…I’ve popped into her life at an interesting time. She happens to be my age, and not every woman our age is thrilled to be single. Plus, I know my CN Tower magnet is on her fridge, being haunted by two Save the Date! cards. (I actually moved them to the freezer side for that picture I took.) I tell her being single is the best. If I wasn’t single, I wouldn’t be in Boston right now, on a date. You can totally create your own destiny. I feel like that’s what I’m doing. If I had a nickel for every time I’ve heard the word “vicariously” lately, I’d be wicked rich. (She authentically uses the word “wicked.” I’m envious it doesn’t sound as normal when I say it.)

While my girl bonding time was awesome, I also have my date to my left. (And my awesome bartender Peter in front of me.) I’m literally one block from home. My date has put absolutely no pressure on me to come home with him. He reads my blog. He knows my sex streak. I’m 1 in 22. I’m batting .045.

But this is the moment in the night… I have to make a decision…

If I don’t sleep with him, he might walk away thinking,

“Fack. I should have taken her to Ikea…”

But I want to sleep with him. He’s great. I’ve had an amazing time. Why not top it off with sex? As I’ve already mentioned, out of town sex is the best. If you’re embarrassed of a one-night stand, you can just come back to your hometown, and say,

“Oh, no… we just made out…”

Or whatever your go to line is, to lie about having sex. But I don’t think it’s anything you should be embarrassed about. So I have one last cab to pay for…

As we enter his hotel, my hooker vibes slightly creep back in, but I laugh it off. It’s not like I’m going to be gone in an hour. (I hope.) The first thing I do when we enter the room is ask if I can take the pen on the desk. I’m a writer and a server. I love collecting pens, particularly ones from hotels. That way if Sarah at work needs to borrow a pen, and “forgets” to give it back, I know that’s my pen. At anytime, I can say,

“Oh is that your pen? Did you sleep with a guy at the Fairmont in Boston too?”

Then, she will hand me back my pen. It’s harder to get your dollar store pens back, because every server has dollar store pens. (God… I’m really stalling getting to the part where I have sex, eh?)

He reiterates once again, that there are two beds, and I can totally just sleep in the other one if I’m more comfortable. So I immediately get naked and throw myself at him. I don’t even keep my bra on, which I usually do because I have such small boobs. Before I’m totally naked, I take a quick Snap Chat and send it to my girlfriends in Toronto.

“Hey ladies! Should I sleep with this dude?”

I can’t believe he let me get away with that. But Snap Chat’s good for that. The video is gone the second it’s seen. (Kinky politicians, take note.)

I don’t know how you picture one-night stand sex, but it’s not always some sort of raunchy sex scene out of a porn. I wasn’t up against a wall the whole night. We were just two people passing through each other’s lives for a night. We crammed in as much bonding as possible, and thus, the sex was amazing. The oral was so facking good too. I actually snuck out of bed in the middle of the night to shower, hoping to receive more oral in the morning. I didn’t want to taste like condom. Maybe that’s TMI, but ladies/gay men, you know what it’s like when you go down on a guy after the condom comes off. Nobody likes that mixed flavour of lube and latex. I think that’s where the term “gag reflex” actually derives from. I’m assuming women taste the same, post condom, so I snuck in the shower. And guess what? My efforts were rewarded! I got more oral in the morning! Woot Woot!

In the morning, he gets ready for work. He irons his shirt, looks for his cuff links… He’s so mature. I check-in on Foursquare, then update Twitter.

We say goodbye in the lobby. I ask the concierge for directions to Trader Joe’s. At least if he thinks I’m a hooker, he’ll think I’m one who uses her money wisely, on really good groceries.

As I walk out of the hotel, I pass by where the Boston Bombings happened. My heart stops a little, as I think of what a beautiful city this is, and how nice all the people have been. My date texts me.

Thanks for an awesome awesome night – had such a great time! Thanks for taking the chance and coming to Boston:) x.


(He wrote awesome twice. That’s no typo.) I smile, and continue my walk of NO shame, up Hanover St. I had a wicked time, Boston. Thanks.

Keep Calm and Tinder on, (in which ever city you choose)


P.S. One last thing about Boston. The walls in the subway are much further away from the trains than Toronto. Every time I rode it, I kept looking out the window thinking I’d see a scene from Pirates of the Caribbean.

P.S.S. So the MORE-ORAL of the story is, always shower after sex. Or the gym. (Those are my rules at least. You’re welcome.)


P.P.S.S. I think you all understand what a “.5” date means now…

  1. walkinsauce posted this