12/16/2013 05:25 EST | Updated 02/15/2014 05:59 EST

My First Date With a Girl

I never mentioned it before, but back in October I changed my match settings to meet women. This 50 first dates series would not be complete without a little open mindedness.

I've never been in a relationship with a woman before, but I have slept with a few. (One of them is still a very close friend.) I'm a firm believer that an orgasm is an orgasm, whether it comes from a man, a woman, or a plastic device that you keep under your pillow. (Santa, if you're reading: throw some batteries in my stocking, please.)

So when a woman FINALLY says yes to me on Tinder, (ladies, what's the deal? Am I chopped liver, or what?) I'm literally giddy. I'm even more excited when she messages me.

Hi Chris:) You look so cute and sexi and happy

I'm not even bothered by the typo. Spelling it "sexi" kind of looks cool. (Plus, phonetically, it still works.)

I am! You're my first girl match! Yay!

I just realized how cocky my message must have sounded. I do NOT find myself sexy, but I definitely can confirm I'm happy. (And so can any of my friends.) She writes back.

Awww. Awesome:)

I want to be totally honest with her.

I don't wanna shock you, but I've been with men too.

She writes back.

It's not a big shock... It's kinda more expected.. Well if you'd like, I'm happy to txt u my cell?

We exchange numbers. After dozens of texts, she eventually just calls me. I'm having a dorky night, so I'm in bed early. I feel like I haven't talked on the phone in bed since I was a teenager. (Especially in such a cute, flirtatious way. Who talks on the phone anymore? I'm all texts.) I'm totally upfront with her.

"I've never been in a relationship with a woman before. I have been with women sexually, and I do find women attractive. I do watch lesbian porn when I jill off. But I'm NOT looking for a relationship. Doesn't matter if you're a man or a woman. I facking LOVE being single!!!"

I'd never say all that stuff to a dude. I'd probably be able to hear the boner over the phone. But for some reason, with her, I could be 100 per cent honest. Plus, I obviously don't want to lead her on. (And it's good to throw the porn thing out there, just in case she knows of something better than the shit I watch on Pornhub.) Now it's my turn to ask her some questions:

"Are you looking for a relationship?"

"Yeah! I want to wake up every morning and make blueberry pancakes for somebody."

Ahhhhhhh! That's pretty cute. (Plus, she is most definitely the first person to EVER say that on Tinder.) I continue asking questions.

"So, do you still date men too?"

"No! Why would I waste my time doing that?"

Bahahahahahahaha! This woman is seriously cracking me up. As we continue to bond, I mention my birthday was on Saturday. Then she says, "So you're a Sag. Awesome."

OMG! She's into astrology too!!!! She tells me she's an Aries, which in case you're a total idiot and don't know, is my perfect match. I totally can't wait to meet this girl. She offers to take me out for a belated birthday dinner tomorrow night.

"Sure! I have a show though, so I wouldn't be able to meet you till 10. Is that too late?"

She laughs.

"What am I, 65? No, of course 10's not too late."

Haha! She's quite sassy. I'm killing myself laughing. We organize plans for tomorrow and I hang up the phone.I feel like we totally bonded. She's even a Jew! As you know, I love the Jews. I'm so excited for our date.I can barely sleep.

The next night, my show starts an hour late. I'm headlining, so I'm locked in until the end. I'm getting very anxious. I feel bad about being late. I text her saying I won't be able to meet her until 10:30. She texts me back: "Okay. But NO later:("

Women. Sheesh. You know I'm going to be one comic to stick to my time tonight. I text her when I'm finished and she offers to pick me up. I haven't let one single man pick me up on any of these dates, but with a woman, I feel safe.

She pulls up in a Zipcar (so savvy), and I literally scare the shit out of her when I say "Hi!" I jump in the car. I'm now officially on my first date ever with a girl. I feel surprisingly comfortable. I don't even need to change the radio station, cuz I already like what's playing. She hands me her phone. (Oh, she's another one of the cracked iphone screen people.)

"Here. I downloaded your horoscope for you."

Cute!!! She's already chivalrous and thoughtful. I'm giddy. She probably thinks I'm a total dork. We drop off the Zipcar in the Queen West area. When we get out of the car, she gives me a hug.

"Nice to meet you!"

She's a very warm person. Friendly, not shy at all (as an Aries would be.) We walk over to the Beaconsfield and manage to score the perfect table for two. It's Thursday night. This could have been far more difficult.

She grabs us a couple of glasses of Pinot Grigio and returns to the table. I can't help but notice how many men are checking her out. She really is gorgeous. Tall, long brown hair... she's even wearing those shimmery black pants that I've been meaning to buy for months. She outshines me in the looks department for sure.

"Sorry for looking like such a skid. I don't like to dress up when I do stand up."

She reassures me I look beautiful. I wore my favourite earrings, which are made from all recycled product. I was kind of hoping she would notice them and she DOES! I am, however, embarrassed of how shitty my nails look compared to hers. I ask if I can take a picture of our hands together. (Mine are the chipped green ones, obvi.)

Bizarre Dating Sites

Our bonding continues. We share stories of past lovers and exes. She has very funny quirky terms for different types of dates. They're dead on. Her observations on the world are so entertaining. I can't stop laughing. I'm having the best time with her.

Then it happens... we're looking each other straight in the eye, and it hits date used to be a man. My date is transgender. I'd be lying if I told you I wasn't a little shocked. I have tons of gay friends, but I don't personally know any transgender people. She's my first.

I have two choices right now. I can either address it and spend the rest of the night asking questions about the transformation, her community, what it's like...


I can just let it go. This is still a date with a person, just like any other date. This date isn't about me learning about transgender people. This date is about me learning about her. And from what I know so far, I think she's great.

So I do it. I let it go...

As our night continues, I get more excited I've met her. She's unique, sexy and fun. I want to express myself on Twitter (drunk tweeting is my worst habit), but I'm obviously new to the transgender world. I write:

"I'm on a date with a tranny and she's a FACKING RIOT! She rocks! See, sometimes you can't just date to fall in love. Sometimes you have to date to have fun."

I immediately get responses from the Twitterverse.

"Umm... you know that word's offensive, right?"

"Don't use the "T" word in your blog. It's a No-No."

Oh my God. I'm embarrassed to say it, but I'm 35 years old and had no idea that that word is offensive. I could have cut this part out of my blog, but I like being honest. I fuck up sometimes. Plus, if I didn't know that word is not PC, many other people may not know either.

I need to pass this message forward, even at the risk of making myself look like an asshole. I don't want to hurt her. I don't want anybody to hurt her. I actually think the most offensive part of that tweet is implying I wouldn't fall in love with her.

Our night continues. I see that two of my girlfriends are down the street at the Dog and Bear (power of Foursquare.) I ask my date if she'd like to go meet them.

"Really? Sure!"

She seemed a little surprised I already want to introduce her to my friends. I don't know why she would be. She's awesome and I know my friends are going to love her. And they do. As it turns out, my date and my friend live in the same building. My friend is obsessed with my date's dog. The four of us continue to drink, though only Coors Lights at this hour. We don't need anything stronger. We sing along to 80's music like it's facking karaoke night. We're all bonding, like a thirty-something version of Sisterhood of the Travelling Pants.

When it's 2:30 a.m. and we all get kicked out of the bar, I say goodbye. I give my date a big hug and agree we have to hang out again. This night has been a true eye opener.

I met her for coffee yesterday. Well, I asked her to go for coffee, but then she took me to the Ritz for cocktails instead. (She already knows me so well.) We've been talking every day since our date. She knows how nervous I am about posting this blog.

"Don't be nervous. Besides, hetero dating blogs are so passé."


"Also, can you call me Chloe in your blog? I like that name."

Done. Chloe continues to talk about relationships and sexuality.

"I don't think people should be labeled as 'gay' or 'straight.' I don't think we all have to put ourselves in a certain social construct. I prefer to think of myself as 'fluid.'"

She's right. We shouldn't be floating around life, looking for the right man, or right woman... we should be looking for the right person. I want to be "fluid" too. I lean over and kiss her. I feel like I might be a more gentle kisser with a woman than I am with a man. I put both of my hands around the back of her head and then I feel something. When we're done making out, I have to address it.

"A hair scrunchy? Really? Do you have to embrace being a girl THAT much?"

"So what?!!! I was just at work, and nobody cares there! Plus, I can't find my black elastic."

Typical girl response...

Keep calm, and Tinder on,


P.S. I want to thank my server Christine from the Hogtown Pub on College Street. I sat alone writing this blog on Sunday night, bawling my eyes out. This was the hardest thing I've ever had to write. Thank you for giving me that Kit Kat.