Adventures of The Not-So Invisible Woman

Last weekend the weather was gorgeously hot and sunny, so to capitalize on the last days of summer I decided to make Sunday a pool day. If you’re not up for swimming in the pacific ocean or one of the several lakes here, you basically have two options: hit up the super posh, oh-so-gorgeous-beach-hotel pool/spa that’s located right on the ocean, or the go to the downtown hotel that’s slightly ghetto but has a decent pool and cheap drinks. Not in the mood to run into a bunch of people I know, I chose the latter.

So, there I was at the ghetto pool, laying out on a pool recliner, enjoying my $6 neon green margarita and remarking on the fact that I’d chosen wisely  (aside from myself, there was only a small group of girls, a two guys and a couple sharing the pool deck = heaven) I was just starting to really get into my book and slip into a deep feeling of relaxation, when I noticed a man and a teenage girl walk into the pool area and approach the group of girls who were sitting in the pool chairs next to me. I looked up from my book and thought,

“Hey, that guy looks kind of familiar”

Then it hit me.


I haven’t seen or heard from Fitness Guy since he stood me up and I called things off. It’s a small town, and I knew that eventually I’d run into him – in fact, I’d been dreading the moment since we parted ways. I just didn’t expect it to happen at that moment….you know, while I was half naked in a bathing suit.

When he sat down three deck chairs away from me, my heart started to race. Luckily, I was wearing giant, oversized sunglasses a la Audrey Hepburn, so he didn’t recognize me right away. I hunched down in my deck chair and furiously texted my best friend:

Fitness Guy is here. With his daughter. What do I do?! Run? Hide?! Jump in the Pool and see how long I can hold my breath?!”

As I waited for her to respond, I tried to calm the pounding in my chest. It took me by surprise because I hadn’t felt this kind of anxiety in months. As I waited for my second margarita to arrive, I gave myself a very angry pep talk.


However, the longer I stayed paralyzed in that deck chair, listening to Fitness Guy talk to the girls next to me (who I learned were his younger cousin and her friends), I realized something: I don’t think he recognized me…at all. You date someone for a few months, see them naked, and yet don’t recognize them in a bathing suit? Is this actually possible?

To test my theory, I dove into the pool, did a few laps and then got out of the pool right by where Fitness Guy was sitting. When I emerged out of the pool, water dripping off my leopard print bikini, I looked directly at him through my dark shades. If there was recognition in the blank stare he gave me, I didn’t see it. Why was I surprised? He didn’t see me when we were dating, why would he now?

When the two guys sitting nearby asked me what I was reading and whether I’d like to join them for a drink, I decided that this was a welcome escape from the awkward situation playing out next to me.

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Actual Conversations From the Other Night

Whenever I’m feeling creatively uninspired, I’ve learned that one of the best things I can do is to step away from my computer, get out of the house and interact with the outside world. Considering most of my nights lately have involved carbs, a blanket and a steady stream of Netflix, I figured it was high time I get out of the house and socialize with someone other than my cat. What resulted, was one of the busiest weekends I’ve had all summer. Friday night I went out dancing for a friend’s going away party, Saturday I spent with my best friend and her daughter, and then the past two days have been spent with my friend Abby who is visiting from Las Vegas. I even met her friend Ethan who is a local blogger out of Vancouver (hooray for new blogger friends!) I’ve had four fabulous days full of good friends, good food & good drinks. It’s been so much fun –  but more on that later!

As I mentioned, Friday night I found myself at a going away party for my friend Gina who is moving to Scotland with her husband this fall. We started off at a friend’s place and after a couple of glasses of wine made our way downtown to Lucky Bar – one of Sleepytown’s better spots. Going out to a bar or club in this town is always interesting because it’s so different than the Toronto night life I am used to. In Victoria, you’ll never get searched & patted down before entering your night spot of choice, $10 will get you a drink for you AND a friend, and you’ll likely see as more girls in flats & flip flops than stilettos (something that I’m still trying to wrap my Toronto-ized brain around). Also you should be prepared for the fact that almost no matter where you go, West Coast Hip Hop reigns supreme. If you don’t hear at least one song by Snoop Dogg, Dr. Dre, 2Pac or Warren G. at some point during the night, something is very, very wrong.

Ever since my self imposed hiatus from online dating, I’ve opened myself up to the possibility of meeting someone the “good old fashion way.” However, I haven’t had much success. A friend of mine told me, “you just need to put out the right vibe and it will happen!” I figured Friday night was the perfect time to test this theory.

So, there I was on the dance-floor, shaking my hips (in my flat sandals) to Dre’s “Next Episode” when a guy we’ll call Bachelor #1 approached me. Bachelor #1 bore an uncanny resemblance to “Thriftshop” rapper Macklemore – right down to the ginger hair and identical haircut.

Bachelor #1:  “What’s your name? Oh, wait – with moves like yours it must be Beyonce!”

Me: “Um, thanks?!” (Repressing hysterical laughter.)

Bachelor #1: Where did you learn to dance like that?

I wanted to tell him the truth – that during a particularly bad bout with insomnia during university, I’d often stay awake most of the night watching videos on BET until a doctor eventually prescribed me sleeping pills. However, instead I decided to keep things simple and replied, “In Toronto”

We stood around talking for a bit until he politely excused himself to go grab another drink.

Although his opening line was undeniably cheesy, if being called Beyonce was the worst that could happen, maybe interacting with the local male population wasn’t as bad as I thought.

Enter Bachelor #2 – a tall, attractive Canadian guy with dark hair. I was nursing a cocktail on the edge of the dance floor when he approached and immediately began speaking to me.

Bachelor #2: I’m hoping you can answer a question for me. Which do you prefer: The Dark Knight or the Dark Knight Rises?

Me: You mean like the Batman movies? Uh, I guess neither?

Bachelor #2: Neither?! That’s an answer I’ve never heard before!

Me: Well, what’s the one with Heath Ledger in it?

Bachelor #2: The Dark Knight.

Me: I guess, I’ll go with that one.

Bachelor #2: A fine choice! Thanks for settling a bet between my buddy and I. BYE!

And like the caped crusader himself, Bachelor #2 disappeared into the crowd never to be seen again.


When I told my best friend this story she commented, “I totally thought he was going to ask you if you wanted to see his Dark Knight rise…because you know, that actually seems like something someone would say to you.”

Throughout the evening, my friend and I noticed that there was this skinny, dark haired guy always lurking right next to us, giving us the eager, crazy eyes.

Friend: “It’s like, every time we’re trying to have a moment, he’s there! I just want him to go away.”

Me: “I know, he just keeps popping up everywhere.”

For the rest of the evening, I dubbed Bachelor #3 “Whack-a-Mole”

Although Gina did her best to shield me from Whack-a-Mole, eventually he cornered me and began to ask me a series of rapid fire questions.

Bachelor #3: “What’s your name?”

Me: “Simone”

Bachelor #3: “What do you do?”

Me: “I’m a writer.”

Bachelor #3: “What do you have to do to become a writer?”

Me: “Go to school”

Bachelor #3: “Where did you go to school?”

Me: “U of T”

Bachelor #3: “How much money do you make?”

Me: “Excuse me?”

Bachelor #3: “Enough to buy me a drink?”

Me: “Definitely not.”

As I walked away, I grabbed Gina and said,

“If anyone asks tonight, you’re my wife.”

From Macklemore to Whack-a-mole,


Next time someone asks me why I’m not dating anyone in this city, I’m just going to send them the link to this post.

How was your weekend?! 

Show & Tell | Swooning at First Sight

As you probably know, trying online dating for the first time was a huge step for me. However, once I started to become more familiar with the world of digital romance, I realized that not only are there a plethora of dating websites, there are now a whole bunch of mobile apps designed to help you date and hook-up on the go. Would I ever use my phone to meet new people? I’m not sure. I was surprised to learn that 80% of Singles prefer mobile dating apps over traditional websites and that 4 out of 5 people would rather use their smartphones to get dates than go online the old fashioned way. Crazy right?

Now enter new dating app Swoon. As mentioned recently Hello Giggles, Swoon is a mobile dating app that brings together everything we love about the internet: anonymity, Facebook stalking and judging people. Just kidding. Not really.

By linking up with your Facebook profile, Swoon helps find cool singles nearby who are interested in you and helps you connect. Because Android users are sexy and need love too, the app is available for both iPhone and Android. All you need a Facebook profile, a dash of optimism and you can get Swooning!

Since I’m still on an online dating hiatus, I thought I would let Joe the Intern try Swoon and tell you a bit about his experiences. Take it away Joe!

“Hey Dudes. Joe the Intern here. As you may know, I’m single and dating. I’ve never tried an online dating app before, but when Simone asked me to test out Swoon and let her know what I think, I answered the call of duty. I linked the app to my Facebook profile and then BAM! I was ready to get started!”

“Swoon shows you photos of singles in your area and gives you the chance to either say “yes” or “no.”  If you both express interest, you’ll be given the opportunity to connect and chat. Within moments of signing up for the app, I was browsing through photos of singles in my area. It was pretty cool because not only was I able to see their photo, I was also able to see whether we had any Facebook friends in common or if we shared any common interests.”

“The best part is the app is anonymous, until a match agrees they both like each other. In the meantime you’re free to browse through photos of singles in your area without anyone knowing. Ellie seems like a really nice girl, but I’m not into girls with more facial hair than me. I’m glad she’ll never find out that I clicked “X” on her photo because that would be totally awkward.”

“I clicked YES for Tanya, but I guess we weren’t a match because I didn’t hear back. I wanted to click YES for Bradley but mostly because I really like his hair and might be a tiny bit jealous.”

“One of the things I liked best about Swoon was that it helped weed out what I believe the French call Les Incompatibles – the people that you can immediately tell won’t be a good match. I know it probably sounds superficial, but attraction is a visceral. If I’ve learned anything from my battle experiences, it’s that you should trust your gut.”

“Instead, you only receive messages from people who are mutually interested, like the very beautiful Mari. When we “check marked” each other, a conversation window opened. We got to know each other a bit and discovered that we both share a love of war novels and Kung Fu.”

“Overall, I enjoyed my Swoon experience and am excited that it might bring me closer to meeting someone special. That special person might even be Mari. We’re meeting up for a Jamba Juice on Friday”

Thanks for the great input Joe!

*This post was brought to you by Swoon. Please note, Swoon is an app for real humans like yourself. All opinions are my own, because that’s how I roll. 

Have you ever tried a mobile dating app? What did you think?

Dickbombing is the New Hello

I finally got Dickbombed the other night.

I’d never even the heard the term “Dickbombing” until a fateful night in Vegas when I was having dinner with all the bloggers at the Paris hotel. Since I was sitting at a different table, I’m not exactly sure of the sequence of events – just that Maxie sent someone a photo of (what I believe was) an animated gif of a penis and then someone else blurted out, “You’ve been dickbombed!” and it stuck. “Dickbombing” became part of my vocabulary. Thanks Bloggers in Sin City!

I’m no stranger to the fact that people send photos of penises to each other. I’ve just never experienced a proper digital dick-bombing first hand or had a catchy phrase to go along with it. Considering a lot of these penis photos are “surprise attacks” dickbombing seems like a much better term than “cock shot.”

Unlike yours truly, I suspect the Queen of Pop is well versed in the art of dickbombing.

According to Dickbombing.comAnyone can Dick Bomb! Dick Bombing is a very inclusive activity with no prejudice against sex or race. Men and women alike can Dick Bomb! School teachers and policemen can Dick Bomb! Waitresses and homeless people can Dick Bomb! Grandmas and uncles can Dick Bomb! Pagans and priests can Dick Bomb! Anyone can Dick Bomb!”

So yes, all you need is a phone, photos of a penis and a dream.

Although I have done many things with the opposite sex, I’ve never electronically sent and/or received a photo of someone’s junk – until now. Why is this a big deal you ask? Because, if you talk to anyone in the dating world these days, Dickbombing is like the new hello. Before I started dating again, I can’t count how many stories I read on other dating blogs that went something like, “I was chatting with this totally hot guy. We agreed to go get pizza sometime, then he sent me a photo of his dick.” Ok, so maybe’s it’s not the new hello, maybe the people writing these blog posts are just dating creeps, but it is a thing. There’s even a Jack in the Box commercial that spoofs the act of dickbombing.

Once again, I suspect Madonna enjoys a good dickbomb every now and then....

It’s a sign of the times. Now that almost everyone has a smartphone (or at the very least, a phone with a camera), people are swapping photos of their genitals with a frequency and ease, unmatched in history. As we speak, cellphone towers are likely transmitting iPhone sized images of penises, in all directions, all across the world. It’s quite incredible.

Under the impression that there are photos of penises lurking everywhere, I assumed when I re-entered the dating scene that I’d encounter some digital dicks of my own – likely, sooner rather than later. However, this hasn’t been the case at all. The men I encountered during my brief foray into online dating seemed way more interested in showing me photos of their boats & seafood they’d caught, than their genitalia – which is probably a good thing.

When I mentioned this to a friend, her response was:

“Really?! I feel like you’re the kind of person who’d get photos of dicks sent to them all the time. Why hasn’t this happened yet?!”

“I know, right?”

Your guess is as good as mine.

...and can you blame her?

When I first started dating again this fall, I was texting with this guy I was seeing at the time. He sent me a message asking if I’d send him a “pic” of myself. I decided to play it safe and send him the headshot I use as my Facebook photo. As I pressed send I thought, THIS IS IT. IT’S HAPPENING. HE’S TOTALLY GOING TO SEND ME A PHOTO OF HIS DICK.

However, much to my surprise he wrote back and said, “Nice! Thx, saved to phone”

Although I was relieved, it made me wonder “Where are all the dicks?!”

That is until the other night, when the thing I had been equally dreading and anticipating all this time, finally happened.

I looked at my phone and thought,

“Well, look at that!”

It could have been that I was looking at an exceptionally nice penis, or the fact that I am quite fond of it’s owner, but it was actually kind of a nice moment.

There in it’s slightly pixelated glory, was the penis – looking tall, proud and one might even say, sophisticated – like the kind of penis that might be known to drink scotch by a fireplace or wear a top-hat every now and then.

It was a flawless dickbombing if there ever was one.

Well, hello there.

However, what essentially made this dickbombing experience a positive one was the fact that it occurred between two consenting adults. No one likes to be surprised by a penis. Therefore, I stand by my belief that the same rules that apply to penises offline, apply to them online. In other words, contrary to what suggests, just because you can dickbomb, doesn’t mean you should. Showing your penis, or photos of other people’s penises to people who don’t want to see them is just creepy. Actually, to be on the safe side you should probably only show photos of your penis to people who have seen it in person and already given it the stamp of approval.

I think Joe the Intern sums it up quite nicely.

In other words, with great technology, comes great responsibility. Dickbomb wisely my friends.


Dickbombing Virgin No More

Have you ever been Dickbombed?


Ask Simone | I Feel Like The Girl From “He’s Just Not That Into You”

Hello & welcome to another episode of Ask Simone where I attempt to answer your questions about sex, dating, relationships & other life stuff. Today’s question comes from K. in the USA.

Dear Simone, 

Ok since you write and are so wise about dating things – I have a question – though the answer is pretty obvious. I met a guy earlier this month (friend of a friend of a friend) and we hit it off the night we met. Really awesome conversation mixed with some old school dancing. Fast forward two weeks later and we go out on our first date. The conversation was awesome again, great back and forth no awkward pauses. We even got dessert. He paid. and offered to walk to me my car. We did the whole “thank you for coming” “thank you for dinner” hug conversation. Then I start backing away to my car…and then I’m like what the hell am I doing. So I walk toward him again, hug it out and then we stop look at each other and smooch. It was total PG stuff because we were in public. So, clearly he didn’t have to pay, walk me to my car or kiss me.

Then last week I texted him, “hey stranger want to grab drinks tomorrow?”  He was booked but said “maybe sometime next week could work” Awesome. I bounced the ball back in his court by asking him to let me know what works for him….annnnnd its been crickets ever since. I understand it’s a busy time for him, he’s leaving his current job to go back for his masters and he’s moving. So maybe he’s just busy. Simone, girl, I’m starting to feel like the girl from He’s Just Not That Into You. It’s pathetic.


Oh, K. Thank you for saying that I am wise even though I don’t really think it’s true! Like you, I’m just trying to figure out all this dating stuff. First of all, let me just say that having read the book and watched the movie (don’t judge me), you are nothing like the ladies in He’s Just Not That Into You because most of those chicks were crazy.  You’re not a crazy. I’ve met you in person I know that you are a smart, sassy, gorgeous woman.

I understand how this situation can be confusing. I’ve been there. Many, many times. It’s so rare that I actually meet someone I’m attracted to. When it happens, I tend to get really excited and I sometimes let extreme optimism get the best of me. There’s nothing wrong with being optimistic, it’s just that sometimes when you want something to work out, you miss certain signals – or at least I do. For example, when I was dating Fitness Guy I wanted things to work out so badly that I think I ignored a bunch of signs that he just wasn’t that into me. It took (literally) being left on the side of the road for it to sink in that the dude wasn’t in it for the long haul. Although I’m getting better at reading people’s signals, it’s a process.

Because of this, I thought it would be fun and helpful to get a male’s perspective on your situation. Luckily I was able to track down my colleague John Drake for a comment. John and I are both Sex Files columnists at Sun Media. As a fellow writer, motorcycle enthusiast and single-man-about-town, I thought John would be the perfect person to ask about this. Here are his thoughts on your situation:

“I’ve been there, it can definitely be frustrating. I’m sure they got along well and perhaps they hit it off but I’m guessing if he hasn’t taken the time to even respond to a text that he didn’t feel sparks flying.

It’s not like he’s being coy or ambiguous – not responding at all is a pretty clear message. Generally if a guy is into you, you don’t have to ask yourself if he’s into you…

Maybe he’ll message in a week saying his grandma died or his dog was in a coma but if I were her I’d move on.

Thanks for sharing John! For more dating tidbits & advice from a guy who knows how to rock a fedora, follow John on Twitter @john_d_drake or read his columns here.

Although it’s probably not what you want to hear, I agree with John. Unless something super serious has happened to this guy, I’d let this one go for now. When I’m interested in someone, I want to hang out with them and make plans as soon as possible – even if I’m super busy. For example, years ago I was seeing this one guy. We’d text often and it was always very flirtatious (bordering on obscene). It was during one of these marathon texting conversations that I asked him, “Where are you right now?” and he replied, “At my grandpa’s funeral” Ok, so clearly this revelation signals BIGGER ISSUES (like, why was even thinking of sexy times with me at a funeral?!) but it goes to show that if a guy wants to contact you he will (even if it’s wildly inappropriate)

As I was reading John’s response,  Joe the Intern took a break from his afternoon push-ups to come over and ask whether he’d be able to contribute his opinion to this post. Since Joe is also single (Yes, ladies. You read that right!) I figured one more opinion couldn’t hurt.

Thanks for sharing Joe! These kinds of situations are hard and I’ve been on both sides of the fence. I’ve gone out with people like The Chef  that I had so much fun with, but there just wasn’t the right spark (and the situation ended in hurt feelings.) I’ve also dated people who clearly weren’t as into me as I was into them. Unfortunately you can’t know what people are thinking or control their behaviour, all you can do is control your reaction to it. Taking a page from Joe the Intern, remember that you are awesome. If someone doesn’t appreciate that from the get-go, then they were never the right person to begin with. In other words, don’t waste the pretty.

I hope that helps!



Did I miss anything? What advice would you give K.?

Got a question for me? Send it here!


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