How to Find The Confidence To Date Again

One of the things people have asked me most often over the years is: how do I get the confidence to start dating again? Let’s be real, breakups not only can leave your heart battered, they can also be a blow to your confidence and self-esteem. If you’ve been reading this blog for a while, it may seem like I fearlessly go from one relationship or situationship to the next, but that’s far from reality. I rarely blog in real time, so often there’s months between a breakup and when I get the nerve to get back on the proverbial horse.

Getting your dating mojo back doesn’t happen overnight. It’s a journey. Here’s a few things that have helped me over the years.

Heal what needs healing.

Even if it’s been a while since your last relationship ended, there’s always emotional stuff that comes up. In my experience, taking the time to reflect, process and heal these sore spots before you start dating again is never a bad idea. This could involve journalling, making art, taking a personal development course, working with a life coachtalking to a licensed therapist (something I’m a huge proponent of!) or working with another kind of healing professional.

Do things that make you feel good in your body.

I have the tendency to get stuck in my head a lot, so taking time to reconnect with my body is something I try and prioritize (whether I’m dating or not). Confidence is all about how you feel. When I move my body, the endorphins flow and I focus less on how my body looks and more on the cool stuff it can do. Whether it’s running, doing a barre class, yoga, using your favourite sex toys or having an epic bedroom dancing session, find what kind of movement feels good to you & go for it.

Pamper yourself.

I’m also a big fan of getting a beauty treatment (or something done) after a breakup and before re-entering the dating scene. Note: you don’t need to change how you look to be a confident dater, but I find sometimes doing the smallest things (getting a haircut, a pedicure or heck, even a new tattoo or piercing) can give you an extra pep in your step.

For example, I recently had a couple of skin tags removed from the base of my neck. I’ve had them for a while and they’ve always bothered me. But it wasn’t until I was on a date recently and the guy actually tried to pull one off (“hey, you have some fluff on your neck. Let me get that!”) and I had to tell him that “uh, that’s actually attached to my body,” that I decided to have them removed for good. Not only does my neck feel ridiculously smooth now, I also (hope) I’ve helped prevent future awkward moments. Skin tugging = not sexy.

(Sidebar: I used to be very anti cosmetic surgery + treatments, but as I get closer to 40 I’ve become a lot less judgemental. I have several friends who’ve had facial surgeries and cosmetic treatments to reduce the signs of aging & they’re happy, bad-ass women who still very much look like themselves. Next time I’m in LA, I may even swing by Dr. Binder to get an anti-aging treatment of my own. At the end of the day, it’s your body. Do whatever you want for you, not for anyone else).

Update your wardrobe.

When you look good, you feel good. Go through your wardrobe. If it doesn’t fit or you don’t feel good in it, donate it. You don’t need a whole new wardrobe to re-enter the dating scene, but it helps if you have a few pieces that you feel comfortable in. Instead of always scrambling before a date, I like to have one or two go-to date outfits preplanned. For example, my go-to fall/winter look is a black dress, tights, ankle boots and a leather jacket. Done.

Take your time. 

When I first re-entered the dating scene after ending a long term relationship (which involved venturing into the world of dating apps for the first time ever), I mistook “not terrible” for “good.” Figure out how you want to feel in your next relationship (for example, safe, supported, respected). If you don’t feel that way with someone, give yourself permission to walk away.

Be kind to yourself.

RuPaul always says, “If you can’t love yourself, how in the hell are you gonna love somebody else!” And while I do think this is true to a certain extent, I think it fails to acknowledge that self-love is a process. Just because you’re still working on it, doesn’t mean that you’re not deserving of love & respect from the people you date. (I used to think that people treated me poorly because I didn’t love myself enough, but the reality is that some people are just crappy. That’s their problem, not yours. End of story.) You’re worthy of being treated with respect, just the way you are. When you remind yourself of this on a regular basis and cultivate a strong sense of self (regardless of where you are on your self-love journey), rejection doesn’t feel so bad.

How to Become Amazing at Talking to Women on the Phone


Want to show me you’re interested? Pick up the phone and call me. Phone calls used to be the norm, but somewhere along the line with the advent of texting, they’ve become the exception. While I’d still prefer texting for most forms of communication, there’s something to be said about the phone call — especially when it comes to catching up with old friends or getting to know a new love interest. I love hearing the other person’s voice and their laughter instead of just their LOL’s. When someone I’m interested in calls me, I get butterflies and my spirits soar like I’m Drake dancing in the Hotline Bling video.

With that said, a lot of people still feel awkward talking on the phone. When the team at Livelinks approached me, I thought it was the perfect oppertunity to share some of my conversation tips for talking on the phone.

1. Invest in a headset.

The biggest complaint I hear from people re: phone conversations is that they “don’t have time to just sit and talk for hours.” I feel you, guys. Unlike texting, where you can distractedly watch back to back episodes of Brooklyn Nine-Nine while you send witty quips back and forth with your crush, talking on the phone requires a bit more mental focus and presence. My suggestion: get a phone that allows you to plug in earphones. I have an iPhone 8 and if I’m planning on making a phone call longer than a few minutes, I attach my headset. This allows me to do other things around the house or even go for a walk while I catch up with my favorite people.

2. Ask open ended questions.

Not sure what to say? Start by asking open-ended questions (I.e. questions that can’t be easily answered with “yes” or “no”) and let them take the lead talking-wise. What are you passionate about? Where have you traveled? This could even be as simple as asking, “what’s new and exciting with you?” In other words, if you’re not sure what to say, make it all about her. Not only will it take the pressure off, it will also send the message that you’re legit interested in learning more about them (always a good thing). If it helps, make a list of open-ended questions before you pick up the phone and keep them handy.

3. Listen actively.

Don’t zone out. If you’ve asked an open ended question and they’ve answered, follow it up with another open-ended question to show that you’re paying attention (“Oh, you traveled to Spain. What was your favorite part?”)

4. Don’t make it all about you.

Ugh. There’s nothing worse than having a one-sided phone conversation where all the other person does is talk about themselves. With that said, if you’re nervous or the other person isn’t saying much, it’s easy to default to stream of consciousness rambling. To avoid turning your phone chat into a therapy session, think back to those  open-ended questions. Make sure you’re asking your phone date questions and giving them the chance to do the same.

5. Don’t overthink it.

Just because you have them on the phone, doesn’t mean you have to reveal your deepest, darkest secrets. Talk to them about stuff you’re comfortable about and just be yourself. Remember, it’s just a conversation.

6. Make her laugh.

There’s a reason why people always list “sense of humor” as one of their most desirable attributes in a partner. Laughter is a huge turn-on. While I don’t suggest you go into the conversation attempting to be a comedian, keeping things light and playful is a great place to start.

7. End the conversation with an ask.

So, the conversation has gone well and now it’s time to sign off. Don’t hang up the phone without locking down the next steps. Whether it’s asking her out on a date or scheduling your next phone chat, make the other person feel like the conversation was a good use of their time by setting up future plans.

8. Channel your inner Winston from New Girl.

Lastly, it all comes down to confidence. I love the show New Girl and my favorite character Winston. While Winston is kind of awkward in real life, we learn in the later seasons that he’s inexplicably good on the phone (and well, it’s pretty hilarious). The point here is that you can be awkward in real life and still have good phone etiquette. Stick to the tips mentioned above and channel your inner Winston. You’ve totally got this!

PS. If you’re looking for a place to try out these new tips, try Livelinks (1-888-507-1136). Thanks for supporting the posts that support Skinny Dip.

On Dating Women & Falling Flat on Your Face


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.


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.

DIY: How To Customize Your Denim Jacket With Pins


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.

enamel pins

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.

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


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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.

The One Where I Attempt To Drink 32 Cocktails in 2.5 Hours

I know some of you probably read the title to this post and thought, “Simone, didn’t you just write a post about how you stopped drinking? So, does that mean that’s no longer on the books?!” Well, yes and no.

A few months ago when I wrote how I had drastically reduced my alcohol intake and started buying art instead, what I should have emphasized was that I didn’t just cut back on booze, I cut back on going out period. While I still spend time with friends regularly, for the most part, my party dresses and stilettos have been gathering dust for the past year.

I’d love to be able to say that this decision was 100% motivated by a desire to be healthy, but that would be a lie. The truth is that I wasn’t just avoiding alcohol, I was avoiding the people I associated with alcohol – namely, Party Guy (remember him?) When I started dating SA, Party Guy and I had an ugly falling out, which lead to another falling out with a mutual friend. While I’m on the path to reconciling with said friend, my falling out with Party Guy was so unsettling that I have zero desire to the him (unless he’s in a burning house fire. Kidding. Kind of. Not really.) So, I’ve been avoiding local social events and bars where he’ll likely be, which is pretty much all of them.

I regularly receive emails from young women who’ve reached out to let me know that this blog has inspired them to be more confident and bad-ass in their own love lives. These emails make my week/month/year. They give me the fuel to keep writing, creating and being a voice that other women can relate to. So, while my health has definitely benefited from not drinking as much, it feels lame to admit that the impetus for this all comes down to avoiding a dude. Not very bad-ass right?

At the time though, it just felt easier to avoid certain social situations than risk running into someone that I no longer felt safe around. Whenever I’d receive an invite for a high-profile social event I’d immediately press delete without a second thought. I was fine with this, until I wasn’t.

Avoiding alcohol in the summer is easy for me. I don’t really like day drinking and I’d rather be up early reading on my patio/at the beach/lounging by the pool than hungover in bed. However, now that Fall is in full swing, I’ve been feeling much more social. When a friend suggested I come with her to Art of the Cocktail, I said yes.

In it’s 8th year running, Art of the Cocktail is a giant cocktail party where you can sample about 35-40 different (mini) cocktails and appetizers from local Victoria chefs, regional distilleries & international brands. I love me a good craft cocktail, so I threw caution to the wind, purchased a ticket, got dolled up in my favourite Tibi skirt & slinky heels; knowing full well that I would probably run into everyone I (wish I didn’t) know that night.

Surprise: I did!

The official theme of the event was “Havana, 1955” but it really should have been “A retrospective of Simone’s questionable dating decisions circa 2011-2014.”

Within the first five minutes of walking into the venue with my lady friends, I saw Fitness Guy (I don’t think he recognized me. Again. Go figure), bumped into Young Dude (we hugged it out because we’re cool like that) before rounding the corner to use the bathroom and coming face to face with Party Guy. After agonizing over this moment for over a year, when it happened it wasn’t that bad. Armed with my favourite red lipstick and some sick finger waves, I was feeling myself that night. I gave him my best resting bitch face – the one that says “I see you but if you want to make contact with me you need to call 1-900-I’mOutOfFucksToGive” (perfected for generations by Eastern European women before me) and kept on walking.

And, it. wasn’t. a big. deal.

It was like the Universe was saying, “we’re going to get all of the awkward stuff out of the way within the first 5 minutes so you can enjoy the rest of your night” because aside from that brief, intense trip down memory lane, the evening went off without a hitch. I had a great time!

I drank and ate all of the delicious things.

I made some new lady friends.

I posed for photos.


art of the cocktail event in victoria, bc

art of the cocktail event in victoria, bc

art of the cocktail event in victoria, bc

I chatted & hung out with SA who was there as well (because apparently, I’ve dated everyone at this party.)

And I got followed around all night by a creepy 60-year man who looked like a cross between Drew Carey and the Glad garbage bag man, minus the charm (because I’m a weirdo magnet ….but seriously, WHY DUDE WHY?)

I finished off the evening with a nightcap of shrimp tacos with my lady friends (new & old.)


(Me: terrible at bathroom selfies)

Originally I was going to wrap this post up with something cliche about facing your fears or how everything is better with girlfriends by your side, but the truth is far more simple. Sometimes the stuff that used to seem like a big deal 1.5 years ago, doesn’t really matter anymore. Also, cocktails are delicious.

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