Dating Archives - Page 2 of 22

I thought it was a high time I wrote an update! First of all, let me start off by thanking everyone for the kind responses to my recent post about dating women. Not only do I feel good about taking this leap in my personal life, I’m also really glad that I took a risk and decided to share it in a really public forum. The responses I’ve received have been really positive and kind. So, thank you.

Although I’m not actively trying to date right now (I’ve kind of put my dating apps on pause mode to focus on some work projects), I do have a few things thoughts to share about my experiences thus far.

Knowledge is power. I hope?

A few years ago I received The Lesbian Sex Bible: The New Guide to Sexual Love for Same-Sex Couples by Diana Cage as a review copy and (ahem) kind of forgot to review it. Originally I was going to pass it on to a queer female friend to review, but for some reason never got around to it – and thank god. This book has been super helpful.

If we’re being completely honest, lesbian sex makes me nervous. I know exactly what to do with men but with women…not so much (at least, I’m worried about not knowing certain things). The Lesbian Sex Bible has been a good resource for answering my questions. I don’t have anything to compare it to but I feel like it provides a pretty decent intro to anyone who is curious about Lesbian sex. And it’s a book! And I’m a book person!

I’ve also learned through my lady dating adventures that not everyone uses lube (let alone owns 6+ different kinds at any given time OR owns sex toys (something I have no shortage of). So, basically if my sex life were an equation it would look like this:

Knowledge & Sex Gear > Actual Experience.

I’m basically the bisexual version of Kenny Fisher from Can’t Hardly Wait, complete with Biggie Smalls references but minus the backpack and offensive braids. And fuck it, I’m just going to lean into it.

I lost my virginity for the second time.

I won’t say too much, just that she was lovely and that the experience was really amazing. I honestly couldn’t have asked for a better first time. It didn’t feel weird or “omg, this is what I’ve been waiting for all my life because it’s so much better than being with men!” It just felt normal and good.

I’m still not very good at reading women and whether they’re interested in me.

Unless they’re being super obvious. Ladies, if you’re interested, let your intentions be known. I’m new here.

Separate bathroom trips are advised.

If you’re on a date with an attractive woman you’re hoping to make out with later, do not decide to go to the bathroom at the same time after brunch. You will end up in adjacent stalls. You will hear noises. It will be awkward. The romance will die. Don’t do it.

The clothing scramble is real.

Trying to locate your clothing in the dark is a lot more confusing when you’re the same gender. This summer was the first time I said after sex, “that looks amazing on you, but I’m going to need my $200 bra that I got for free from the internet back.”

Just because you find someone beautiful doesn’t necessarily mean you’ll be attracted to them.

After going on a handful of good dates with some really lovely women, I started to feel like maybe something was wrong with me because these dates were very chaste. Very little touching, no goodnight kiss – even after several dates. This is very different from most of my experiences dating men. Were we just friends? What was going on?! These women felt impossible to read. Looking back, the answer was obvious all along. We just didn’t have any chemistry…and I have the feeling they felt the same way about me. It took meeting someone I actually had chemistry with to realize this.

If there’s one creepy straight dude at an LGBT event, he will find me.

EVERY. DAMN. TIME.

And he’ll lurk like the seasoned lurker he is until Rhonda who does bodybuilding comes over and tells him to hit the road.

Because, you know, this is my life after all.

Last month, I was sliding head first down a pole and landed flat on my face. And you know what? While it was embarrassing and uncomfortable for a moment, I’m fine. I posted on Instagram that it reminded me of something important: in fitness and life, falling on your face happens but it’s not the worst and you get over it.

Since the beginning of the year I’ve been steadily taking pole dance classes. I’ve advanced from the beginner to intermediate classes – but in June, I decided to try an advanced level class. My instructor assured me that I’d be alright in a higher level class, but I was nervous – and for good reason. The advanced pole classes were a lot more challenging (hence, the face-plant) and I went from being one of the better more experienced people in class to one of the worst. My body aches after every class and I’m covered in bruises. Weeks will go by where it feels like I’m making zero progress and everything is just hard, but then something will happen – a new move will come easily or I’ll finally get the hang of one tiny element of a combo and it will renew my faith in the learning process. It’s exhilarating but also deeply uncomfortable, but I keep showing up anyways. Did I mention that all of this learning happens while wearing little more than a bathing suit?!

I’ve been thinking a lot about this process and realized something about myself: I don’t like doing things that I’m not good at. I can be a total ham and a bit of a show-off, so I tend to only gravitate towards activities where I can shine. That’s part of the reason I like my barre classes – with 15 years of ballet training under my belt, I’m confident I won’t embarrass myself and literally fall on my face.

I’ve noticed this pattern outside of my fitness life as well. I gravitate towards hip hop and house music nights partly because I love the music and know how to move to it (thanks all of those insomniac nights I spent in university watching music videos on BET!) and avoid Latin clubs even though I enjoy the music (my salsa moves are “meh”). I write about dating and relationships professionally because I’m good at it even though, sometimes – ok, often – I think about breaking out of the niche I’ve created for myself. And I date men, because men have been approaching me since I was 12 years old (#creepy, but that’s another post altogether), getting their attention is rather easy and I like dating men – well, mostly. With the exception of hip hop & house music (which I’ll never give up), these activities provide me with validation but don’t necessarily satisfy me or help me grow.

In January I decided my word for 2017 was going to be “shift” so, I’ve embracing that and making a few changes.

[VERY DEEP BREATH]

I’ve decided to open myself up to dating women, as well. For some people this may be a huge surprise (I’ve spent the past 8 years writing a very hetero blog) – for others who know me in real life, maybe less so. This decision isn’t spur of the moment, but rather years in the making. I’ve been attracted to women since I was in my early 20’s, but never really did anything about it. This is partly because I was always dating men and wasn’t sure how to even go about trying to date women, but it was also because I was scared – not of what my friends and family would say (they’re very openminded and supportive) but rather how people who aren’t close to me would perceive my actions. It’s like I could almost see the comments section (“a dating writer who banged a bunch of dudes and now is dating women…how cliche” or worse, “she’s just doing this for a good story/blog fodder.” )

And yes, I realize how ridiculous this sounds. When I told a friend and colleague about this, she said, “it’s none of their business. Fuck the haters!” and reminded me that people have been making erroneous assumptions about me for years. True.

Plus, I haven’t wanted to define myself with a label. I’m still physically attracted to men, but lately I find myself more emotionally (and in many ways, physically) attracted to women. So, I feel like this is an unanswered question that needs be explored.

So, why am I sharing this now?

Because I’ve learned something over the past month. While I’m extremely confident (to the point of almost being cocky) with men, I’m hopelessly bad at dating women. I’m shy, I’m awkward and I have no idea what I’m doing. It feels a bit like I’ve gone back to square one and I’m back in high school again. But like the pole class that kicks my ass on a weekly basis, I keep showing up anyways – for better or worse – because I know there’s something for me to learn here.

Sharing my thoughts through writing is how I process things. So, while I won’t be providing play by plays of the dates I go on or the people I meet while dating in Victoria, I’ll probably be writing about my general thoughts and experiences throughout this journey.

Spoiler: talking to women on Tinder is a thousand percent better than talking to dudes. You know, in case you ever wondered.

This post has been brewing for awhile. Today we’re going to talk about text messages. Gross, disturbing, overtly sexual, inappropriate, creepy and uncalled for sexts.

But, before we get to that we need to talk about The Actor. I don’t think I’ve ever mentioned him, which now seems like a major oversight.

The Actor and I met in 1999 while we were both working at an upscale menswear store in downtown Toronto (one of my first part time jobs when I moved to the city.) Although we only worked together for a short time, he made an impression on me. He was studying pre-med and seemed kind & thoughtful. He was also cute – in a rather unsettling way.

The Actor and I look alike. Scarily alike.

In fact, when we were introduced my first thought was, “if I was a man, I would look exactly like him.” He has a porcelain complexion, blue-green eyes framed by dark expressive eye-brows and a thick mop of curly dark hair. Although my hair at the time was dyed a frosted blonde (hello, it was the late 90’s), other people noticed the resemblance too. A bunch of my coworkers just assumed The Actor and I we were related. On several occasions people asked me in earnest if he was my brother.

I’d have to explain, “Oh, you mean ________? Yeah, we’re not related.”

Coworker: “Are you sure?”

Faux familial ressemblance aside, The Actor and I had a connection but I never pursued anything with him because I had a boyfriend at the time. We both stopped working at the menswear store shortly thereafter.

Flash-forward a year later: I’m now single and attending the same university as The Actor where e’d periodically bump into each other around campus every few months. At the end of third year, I ran into him while on the way to my summer school class and we ended up having an extended stop & chat. He told me he had been doing some acting. I assumed he had (like me) shot a few low budget student films. We exchanged numbers and agreed to hang out (finally!)

I was at the video store near my apartment when I saw the poster. The bottom half featured a dark haired man and woman in bed. Above the image: a 2-ft wide set of eerily familiar blue-green eyes. It was The Actor. The movie he had starred in wasn’t some run of the mill student production, it was an award winning film by a world renowned director. I was stunned.

The Actor was kind of a big deal.

A few nights later we went on our first date to a popular upscale pub located near campus. We sat on the patio and the conversation flowed nicely. At this point in my dating career, I was used to spending time with sullen, sardonic, troubled dudes (read: douchebags), so The Actor’s disposition caught me off guard. He seemed legitimately happy and excited about everything – including hanging out with me.

At some point during the night I got up to use the washroom and was accosted by two girls.

“Are you with ________?” they asked.

“Yes, we’re having a drink.”

“Oh my god, he’s so dreamy,” one of them said.

“Uh, yeah, I guess” I replied.

“You know he’s like a total player right?” the other one said.

“Uh?”

“Yeah, you should be careful. He like, totally broke two of my friends’ hearts.”

All I could think during this interaction was, “THAT GUY?! REALLY?” Sure, he was adorable but The Actor just seemed really sweet and kind of hapless. I was well versed in dating players and he didn’t strike me as one.

I politely assured them that I could handle myself and went back to our table.

I was dating several different guys that summer. When I told my best friend this story, she said, “really, he should have been worried about you.” She has a point.

We went out 3 or 4 more times, during which we had a few make-out sessions. On our second to last date, I invited him back to my place. We were kissing, when he pretended to lose his balance, pulling me onto my bed. It was a move out of…well, a movie (and not a good one).

We kissed some more but I stopped things before they went too far. Maybe it was his cheesy make-out move, his exuberant (bordering on slightly manic) energy or the fact that WE LOOKED RELATED, but something felt a bit off. Although I liked The Actor, I decided to hold off on sex until I could get a better read on him.

A few weeks later, I went back to the West Coast for the summer. In September, he invited me to be his date at the Toronto Film Festival Holt Renfrew party, but I had a terrible case of bronchitis and couldn’t go.

(My Mom is still mad at me for this and insists I should have just “sucked it up and went.” She’s always been a fan of The Actor and sees him as “the one that got away.” She never misses a chance to remind me of this whenever she sees him in something on TV.)

The Actor and I lost touch for a few years until we found each other on Facebook. By that point he’d moved to LA to pursue acting full time and I was in a serious long term relationship.

There have been many times between then and now that I have thought back on what did, or rather what didn’t happen between me and The Actor. Was I really not into him, or was I just turned off by the fact that he seemed too nice? Accustomed to dating assholes, I used to think that nice guys were corny. However, now that I’m in my 30’s and a little bit wiser, a corny guy actually sounds pretty great.

So, when The Actor reached out to me on Instagram a few months ago, I was intrigued. He’d noticed photos from my recent trip to Los Angeles and mentioned that we should hang out next time I was in town. We exchanged numbers and he texted me that night.

Maybe I was being totally naive, but that evening I allowed myself to daydream about what our time in LA might look like: afternoon bike rides along the Venice boardwalk followed by dinner & drinks at Sugarfish. This could turn into the perfect vacation fling…. or maybe something more? Was The Universe finally sending me my very own Canadian/American Angeleno Dream Man?!

However, NOTHING could have prepared me for what came next.

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Unlike Christian Grey, no one has ever referred to my interests as “singular.” I love Tupac Shakur, The Muppets, Ta-Nehisi Coates and 80’s kitsch in equal measure. I’m fairly well read. I can quote Foucault and the movie Wayne’s World – sometimes in the same sentence. My dream Jeopardy category would be “obscure R&B groups from the 90’s” and I’ve read a shocking number of Eric Jerome Dickey novels, considering I’m a white lady.

My interests have definitely confused some of the people I’ve dated. I can’t count how many times a dude has said, “huh, I just don’t really get you.” I used to feel insecure about all of this, but as I got older I realized that there’s no glory in hiding from the world who you really are. My dating philosophy is now “take me as I am” – Joe the Intern, 90’s hip hop references, incessant quoting of Mike Myers & Liz Lemon and all.

A few years ago I promised myself that I would ‘do more of what makes me awesome,’ so lately I’ve been looking for ways to embrace my diverse interests. That’s how I ended up falling into the offbeat accessory vortex that is pin-culture.

It started with a plain vintage denim jacket and a single Prince pin that I purchased a year ago from Georgia Perry (after seeing a bunch of her pins in LA.) After receiving that first pin, I quickly discovered a whole online community of independent artists and pin-makers. My love for pins has since blossomed into a full-on obsession.

You guys, there’s a pin for everything! From 90’s hip hop and tacos to politics and feminism, I’ve finally found a way to wear my interests. Plus, I love that my pin obsession allows me to support small businesses, artists and social justice causes. Along with making gorgeous, timely pins, companies like Radical Dreams donate a portion of their sales to community organizations.

Here’s what’s currently on my jacket (clockwise)

1. Madonna (vintage – Ebay) – Although I’m not really into current Madonna, 80’s and 90’s Madonna has been my jam since childhood. This vintage pin I found on Ebay looks like the kind of thing middle-school aged Simone would have envied on older, cooler teenagers.

2. Prince (Georgia Perry) – My very first pin! I love, love, love Georgia Perry’s playful artwork.

3. TacoBelle (Hannah Nance for Yesterdays) – Well, this is just fitting.

4. Please Adopt! Cat Pin (Studio Coup via Vancouver Cat Cafe) – Black cats are the least likely to be adopted. As a black cat owner, this makes me sad because they’re great. Let’s change this.

5. Mars Investigations (Good Good Pins) – Who’s a huge Veronica Mars fangirl? *Waves Hand*

6. Leopard Pin (Charlotte Farmer) – I love Farmer’s illustrations & this cat-centric pin charmed me.

7. Selena (Mi Vida) – I discovered Selena Quintanilla-Pérez while listening the radio during my first trip to California as a teen & was hooked instantly. I thought this pin was such a great tribute to her. RIP.

8. Prince (Pin Jong Ill) – Fun fact: I bought my Mom a matching pin for her leather jacket.

9. Princess Carolyn (Alleycat Graphics) – A huge BoJack Horseman fan, I was tickled pink when I discovered a pin of my cartoon alter ego. This one is perfect for those days when you need a pep talk.

10. Double Double (Fair Goods) – Canadians get this one. The “double double” at Tim Hortons isn’t just a coffee order, it’s a way of life.

11. Peeno Noir (Lady No Brow) – Are you a fan of the Unbreakable Kimmy Schmidt? Me too. Pinot Noir Caviar, Myanmar, Mid-sized car.

12. Horsey pin (Lisa Hanawalt for Big Bud Press) – Lisa Hanawalt is the lead art director of BoJack Horseman and she designed this pin.

11. Wayne & Garth (Fair Goods) – See above. This feels… essential.

12. Madonna (vintage) – This is actually a pin I bought & wore as a tween/teen. I’m so glad I kept it!

13. Black Lives Matter (Radical Dreams) – Because the world needs a reminder.

14. Sade (Pintrill x Deerdana) – I adore Sade. She’s one of my all time favourites. This artist collaboration pin is gorgeous.

Here’s some of the pins I’m hoping to add to my collection in the near future:

1. “None of my business” Kermit – My favourite amphibian and my favourite meme…together at last!

2. Laughing Obama – On the outside I’m laughing Obama, on the inside I’m crying.

3. Aaliyah (& her 4 page letter) – another one of my high school favourites immortalized in pin form.

4. Amy Winehouse – Yes, I have a lot of pins of dead celebrities. No, I’m not sorry.

5. Taco Truck – This one also seems self-explanatory.

6. 2 Pac – #NECCESSARY

7. Liz Lemon – It’s true, Liz Lemon really is my spirit animal. There’s also an adorable Mindy Kaling pin.

8. Jem – Before my Madonna obsession, there was Jem.

9. “Pancakes” – Yes, that’s Dave Chapelle as Prince. This pin combines two of my favourite famous dudes in a hilarious ode to one of my favourite Chapelle show sketches.

10. Living Single – I was obsessed with this show in high school. It stared Queen Latifah & was like Friends but better. Considering I’m actually living single, it seems more relevant than ever.

11. George Michael – My family are also big George Michael fans. I’m really saddened that I’ll never be able to take my Mom to one of his concerts.

12. The Golden Girls – I have a theory that if they keep making Sex & The City movies, it will eventually just turn into The Golden Girls, but not as good. Hashtag Squad Goals.

13. The cast of The Wire – Because, reasons. Sadly, Omar is not included in this set.

14. Yo! MTV Raps – the perfect accessory to my Yo! MTV Raps collector cards.

15. Bluth Banana Stand – There’s always money in the banana stand.

16. Because having two Prince pins is not enough & this pin is epic.

My goal is to get to the point where I can just point to my jacket whenever someone I’m on a date with asks,”so, tell me about yourself.” That’s the dream, my friends. I think we’re almost there.

PS. If anyone ever buys me one of these, my heart will be theirs forever.

For more Pin-spiration, make sure to check out my Pinterest board devoted to pins and follow me on Pinterest.

As you know there’s a holiday tradition that fills mailboxes, mantels, refrigerators and walls in homes everywhere; it’s the annual holiday card. I admit, I love a good holiday card. It’s the chance for people to show pictures of their families and offer a few life updates. (Now that I’m in my thirties, at least 50% of the cards I receive feature the gorgeous, smiling faces of my friend’s children. Usually there’s a Santa suit or three in the mix.)

While I love receiving these kinds of cards from my friends, I always feel weird sending my own life updates and I’ve never made a personalized photo card. I’ll usually just pick out a few cards from a local shop that I think look cool (case & point: last year I sent Almie a Nick Cage themed card) and include a quick note of love & appreciation before I pop them in the mail. Don’t get me wrong, my life as a single 30-something is actually quite awesome, but I’m afraid that an official “this is what I did in the past 12 months” update might come off as boastful or just silly.

Do my friends with children really want to hear about the 2.5 weeks I spent galavanting around Los Angeles, shopping, going to shows and eating every taco in my path? Will my lifestyle just come off as selfish and indulgent? Do they want to see photos of Joe and Hammer in tiny ugly Christmas sweaters*?

I think a lot of these feelings come down to the fact that once you reach a certain age and are single and/or childless, society subtlety (or not so subtlety) suggests that your life isn’t as valuable as the lives of people who are partnered and have children. This needs to stop.

(* if the answer is “no” to the tiny Christmas sweaters, we should probably end this friendship right here right now.)

Match noticed and they think singles updates matter too! This year they’ve created a unique set of holiday card templates just for singles so they too can join in this tradition and spread extra holiday cheer.

Here at Skinny Dip, the staff and I have made our own Singles Greetings cards. Mine is all about food, naturally. You can see Joe and Hammer’s below.

Want to make your own card? You can do it here!

May your holidays be amazingly delicious and devoid of rap beefs.

Simone

This post was sponsored by Match.com. Thanks for supporting the brands that support this blog.

I’m Basically the Lesbian Kenny Fisher & I’m OK with That

Knowledge is power. I hope?

Knowledge & Sex Gear > Actual Experience.

I lost my virginity for the second time.

I’m still not very good at reading women and whether they’re interested in me.

Separate bathroom trips are advised.

The clothing scramble is real.

Just because you find someone beautiful doesn’t necessarily mean you’ll be attracted to them.

If there’s one creepy straight dude at an LGBT event, he will find me.

On Dating Women & Falling Flat on Your Face

Guys, We Need To Talk About Your Texts

DIY: How To Customize Your Denim Jacket With Pins

Make Your Own Singles Greetings with Match.com

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