Guest Post | On How to Be Single

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Going through a breakup? Our intern Kaitlyn bravely shares her story today about what it’s like to find yourself single after being in a relationship for 7 years. Take it away Kaitlyn! (illustration credit: Erick Davila)

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I‘ve realized that I do not know how to be single. Not just single –  but independent.

I knew this year was going to be filled with challenges. I’m attending a school where I don’t have any friends and my lover is attending a school two hours away. I knew what I was up against from the beginning. Or so I thought.

The first three months of college were great. I had my own little group of friends, something I’ve always wanted. It was a huge self-esteem boost, because thinking back to high school, I didn’t really have friends there either. In hindsight, it was my fault. My lover didn’t approve of my preference for guy friends over girls. When I finally did make a really good girlfriend, I heard rumors about how some of her life choices weren’t the greatest. I distinctively remember thinking “it’s her life, I’m not going to let it affect mine” and I didn’t. I remained her friend for as long as I could, but eventually time and distance pulled us apart.

Going to college was the fresh start I needed. I woke up every day and actually looked forward to going to school. It was my little group against the world. We were constantly going out and making the best of everything and anything. However, as the saying goes, “don’t cross oceans for people who won’t cross puddles for you.” Gradually, my little group got smaller. Three amigos turned into two. Can you even have two amigos? Can my dog count as the third?

Now it’s just me and my roommate.

And of course I still had my lover. Key word had.

As my group got smaller, I found myself back at square one. I hated waking up every morning to go to school. The thought of it made me sick to my stomach to the point I would cry myself to sleep every night because it felt like I just couldn’t continue. All the independence I had gained when I moved was gone. Just. Like. That.

I dragged my roommate to my lover’s college. I was hoping that I could convince her to leave with me and start over at a new school.

That weekend, we toured the college and living arrangements. But, when I met up with my lover he told me, “I don’t want you to start over. Also, we can’t live together because I need to live with my friends for assignments and I don’t think they would be okay with you being there.” So yeah. Ouch.

Now is a good time to mention that I have been struggling with depression since grade six. My lover had rejected me. I was pretty close to failing half of my classes and I didn’t have a support system at school. Cue: depression.

I slowly began cutting myself off from life. First was my school and the teachers. I had no motivation to be in class and just felt was numb. I was a zombie. Wake up. Go to school. Go home. Sleep. Repeat.

And then something happened. More so like someone.

An old high school friend that is one of my roommates.

We’ve experienced similar yet different challenges that have defined who we are today.

As much as I hate to admit it, I live in the past. I’ve carried the past with me because I thought I needed a constant reminder that “this is the shit that got you here” or “this is how things were back then and how they need to be now.” My past hurt was my anchor. I thought that if  I let go of it, then I might fall backward. The irony being, that hanging on to this emotional baggage is what’s kept me from moving forward.

I was bullied and a bully. I was abused emotionally and physically. Because of this, I feel like I carry this incredible weight on my shoulders to get everything right; to be the kid in the family that has the “perfect” life. You know the one where you go off to school, get a kick ass internship (thanks Simone!) find the love of your life, settle down, get married and have babies. Just kidding re: the babies. I don’t want human babies. Or do I?

My roommate is one of the happiest people I know despite everything life has thrown at him. He’s inspired me to not only to let my bygones be bygone, but to grow as a person and to be the best that I can be.

Remember when I said I “had” my boyfriend? As of a week ago I am officially single for the first time in seven years.

I loved him and wanted to spend the rest of my life with him, to the point where we were talking about engagement rings and future plans. But, he was a crutch. He was my crutch. Someone for me to lean on. I depended on him to tell me what I needed to do, even though I didn’t always agree.

We skyped. I cried, he cried and then we were free.

A weight has been lifted off my shoulders. My lover and I both had very different priorities this year. His top three priorities were: school, money, friends, job. Mine on the other hand, was our relationship. I wasn’t on his list of priorities and for some reason I thought this was okay. Now I know that it’s not.

I told him I need time for me. I need to figure out what I am meant to do and how to do it. I knew that if I stayed in the relationship any longer I wouldn’t have the strength for the soul searching I so desperately need to do in order to begin the process of healing and moving on from my past.

“You have to hurt to heal,” a wise man once told me.

So here I am in the first time in seven years, single, on a journey of self-discovery and learning how to be independent. Wish me luck!

When a Whisper Turns To a Yell

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Whether it’s going to your first music festival or finally writing your first book, one of the things I’ve learned over the past year is that good things happen when you push past your comfort zone. When I started this blog in 2009 I chose the name “Skinny Dip” because I thought “skinny dipping” was a good metaphor for writing about your life online – it’s naked, it’s scary but also a hell of a lot of fun.

While writing about pretty things & sexy goodies is definitely enjoyable, lately I’ve been feeling a little too comfortable around here – and not in a good “hey I’m wearing silk pyjamas” kind of way. It’s more like, “hey, I’ve been sitting around in these silk pyjamas so long that now there’s a bum shaped imprint on the couch.” It’s time for a change.

I want to use this space for it’s original intention: to tell the truth – about dating, about sex, about bodies, about the challenges of being a (now) 30-something woman & writer. I want to talk about it all, in the most honest way possible.

So, in an effort to strip things down, I’ve decided that every week I will write and post one short personal essay about something that is currently ‘true’ in my life. There’s a very good chance I’ll still post things in-between these mini-essays, but in the meantime I’m really looking forward to more writing and real talk. I hope you are too.

Here’s the first of those “truth-bombs” if you will.

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When I was in college, I was an avid “recycler” of relationships (Al Gore would have been proud!) My love life mostly consisted of a rotating cast of 3-4 different guys that I’d keep getting back together with even though all the signs were there that none of these relationships would ever work out, no matter how many times I revisited them.

This has always been one of my favourite quotes from Maya Angelou (she has so many.)

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At the time, I understood on an intellectual level what Angelou was getting at, but I just couldn’t put it into practice – not really. So, I continued to recycle my hookups and date my exes even though we’d “broken up.” I justified my behaviour in two ways:

“If I’m recycling relationships then it means I’m not adding any more notches on my bedpost.” (I was very concerned back then at being perceived as a slut. Now, as a 30-something, I couldn’t care less.)

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“If we keep coming back to each other, it must mean there’s something there.” (What I know now: there’s always something there. That doesn’t mean it needs to be revisited.)

I’d keep up this pattern until something would happen that was so hurtful and ridiculous that it would be impossible for me not to walk away (i.e. discovering the person I was dating had a secret family stashed on the other side of the city.)

The whispers were always there, quietly guiding me towards the knowledge that these people were wrong for me. But, I needed that whisper to turn into a yell before I’d pay attention. I can’t help but wonder how much pain I could have spared myself if only I’d really listened to what the people I dated were telling me.

(For example, “I don’t want a relationship right now” doesn’t translate to “I just need the right woman to change my mind.” Trust me.)

I’m much better now. I’m becoming better at listening to those whispers and I don’t let things linger like I used to. I favour clean breaks and moving forward. Yet, in order for that clean break to happen, I still need definitive answers. I need to know that a situation is unequivocally wrong for me so I can eliminate it once and for all from my psyche – or, as my Mom likes to say, “Simone, you can’t just leave well enough alone.”

Since I broke up with The Secret Agent, I’ve been turning over stones looking for answers. This is how I ended up on a date with someone I hadn’t seen in 14 years.

I fully, 100% blame Adele’s Hello for everything that happens next (only kind of sort of kidding.)

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I met C. in 2001 through a friend. He was everything that the guys I had dated previously weren’t:

Big hearted. Sweet. Cheerful. Devoted. Tall. (Although he’s made it clear that he wants to be played by Idris Elba in the movie of my life, I envision him as more of a approachable, Pooch Hall type.) He’d do nice things like make me tapes with remixes of all of my favourite Prince songs – just because. He was the kind of guy I should have been dating all along – that I’d be super excited to date now. However, unfortunately,  at the time I was still attached to the immature and misguided notion that a relationship needed lots of hot and cold drama to be “real.” I thought C. was “too nice.” So, a month or two into dating I broke things off (something I’ve always felt bad about.)

Now, flash-forward fourteen years. I’m browsing through my OkCupid matches when low and behold, I’m matched with C.

As it turns out, he’d recently moved to the West Coast from Toronto. Messages were exchanged, texts were sent, but it didn’t go anywhere. A few months later, I met & fell in like with The Secret Agent.

Flashforward 8 months and I’m single again. I reached out to C. to say “hello” (cue Adele.) A few weeks later, I found myself sitting across from him at a sushi restaurant in Vancouver, laughing and having a really great time. This lead to a second date, a third date and a four day weekend spent together.

I like myself a whole lot more than I did when I was 21. Consequently, I like the 2015-2016 version of C. better too. He’s the same friendly, affable, cheeky guy that I initially got to know – but better. He also still does sweet things that I like (ie. records the Soul Train Awards and doesn’t “cheat” & watch them until we’re together.)

But, here’s the thing about those whispers. Once you become attune to them, they become impossible to ignore. Although C. and I connected in ways that were new and pleasantly surprising, there were a handful of little things that pointed towards the fact that long term, we’re probably not a good match. I spent years thinking that the reason that we didn’t work out the first time was largely due to my own immaturity, but really, the whispers had been there all along. Once I noticed these things, I couldn’t un-notice them. Before I knew it, the whisper had turned to a yell.

I called things off. Again.

We talked and agreed that neither of us regret reconnecting. And I truly don’t – regret it that is. In this case, I’m glad that I revisited the past but I’m also glad that I listened to my gut.

This is all to say that sometimes we need to turn over those stones. You might not always get the answer you were hoping for, but if you pay attention, you’ll always get the answer you need to move forward.

On Bromances, Breakups & The Stories That Bind Us

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When I start dating someone new I have to “come out” to them about a lot of stuff. For example, that I write about sex & relationships on the internet, that I live with my mother and that I have an anxiety disorder (I usually save the last one until I’ve had a chance to get to know them.) However, since bringing on Joe the Intern in 2013, if they’re OK with all of the above, then I have to add, “Oh and by the way…I also have an “employee”  who is a 12 inch tall half naked man.” You either get what Joe is about or you don’t. But, if you are going to date me, you need to know that me and Joe are a 2-for-1 package.

One of the things that initially impressed me about The Secret Agent was that he wholeheartedly embraced the presence of Joe the Intern, right from the beginning.

A few days after our very first date, The Secret Agent was scheduled to go on a business trip. He texted me from his destination and asked, “Is there anything that you or Joe need from the mainland?”

I told him I was good, but sent him this photo of Joe just for fun.

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He came back from his business trip with a box of jellybeans for Joe and I to share. This was the start of what would be an epic bromance between the Secret Agent and Joe.

Actions speak louder than words. By accepting Joe into his life, The Secret Agent made it clear that he also accepted my quirks – a sign that he was the right person to have in my life.

After that initial offering of jellybeans, The Secret Agent and Joe would exchange messages on the regular.

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And, like any Step-Boss trying to impress his lady, he spoiled both of us rotten. He made sure Joe & Hammer kept their fanciness on fleek with a pair of jaunty top hats. He also purchased Joe a tiny pair of vintage cowboy boots and generously donated to the Skinny Dip vehicle pool, much to the delight of the interns.

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To show his affection for Joe, The Secret Agent even went so far as to get this T-shirt made for our adventure at the Squamish Music Fest.

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However, it’s not about the material things that The Secret Agent brought into the relationship, but rather, the unending patience he showed for my unconventional hobby/intern. He travelled with Joe, helped me shop for props and never complained when I had to do multiple takes of the same photo just to get the perfect shot (doll photography is a lot harder than it looks!)

I know if you asked the The Secret Agent, he’d tell you that he doesn’t just tolerate Joe, he truly enjoys spending time with him and helping with the photos (& disposing of um, “personal items” in elaborate ways.)

While we were California, we used the bikes provided by our airbnb hosts and spent an afternoon riding around Venice beach & Santa Monica. When I looked up at The Secret Agent riding ahead of me on the boardwalk and saw Joe’s tiny head peeking out of the top of his cross body bag, I not only smiled – I felt grateful to have S.A in my life.

As I’ve explained before, The Secret Agent and I are alike in some ways, but also very different in others. Despite differences in lifestyle and ways of being, a shared affection for Joe was always a constant in our lives.

Whenever these differences became impossible to ignore or silence crept into our conversations, there was always Joe, standing by to break the tension.

The Secret Agent would ask me, “What do you think Joe’s up to right now?”

And I would reply with something like, “Shhhh, don’t break his concentration. He’s telepathically communicating with Hammer about all the margaritas they’re going to make tonight.”

That tiny 12 inches of muscled plastic was the glue that held us together, until it was no longer enough. 


I’ve always thought that the worst parts of breakups aren’t the actual moment of the split, but rather the weeks, days, hours leading up to it. When you stop holding hands in your sleep. When texts that used to be signed by “xoxox” are now signed with happy faces instead. When kisses on the lips are replaced with kisses on the nose. When you start feeling more like friends than lovers. You try and convince yourself that you’re just imagining these things; that you’re reading too much into it, despite the fact that evidence to the contrary is staring you right in the face.

These are the moments that suck the most.

This is all to say that The Secret Agent and I broke up about a month ago.

While it’s always sad when something ends, I don’t have any regrets when it comes to my relationship with The Secret Agent. Unlike my relationships in the past, which involved a lot of self-sabotage and trying to force square pegs into round holes, I’m proud of how I handled us being together. I committed, I was patient and I let the relationship evolve organically – we both did. We had a great few months together, but when those differences became too big to overcome, we parted ways as adults without any drama.

{Epilogue} I’m fine. The Secret Agent is fine. Joe is fine. The Secret Agent & Joe have decided to stay in touch and continue being “bros.” Joe is handling it all like a champ, with his signature brand of stoic silence.

(Top photo is via Steven Henke‘s series, “Barbie Does Palm Springs“)

Sex, Lust and Ruskie Business

Since writing this post several of you have reached out and requested more dating, sex and relationship stories. I often don’t write in real time, so here’s one from my personal vault – circa a few years ago. 

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Recently, a friend and I were discussing the topic of hooking up with people in other countries.A few minutes into the discussion I realized that my foreign boot-knocking experience is actually surprisingly limited. I never did the whole backpacking through Europe thing (everyone who did, seems to have some story about hooking up with a hot Spanish dude in a hostel), I’ve never been to an all inclusive resort and I was too broke in university to spend a semester abroad. All of my international travelling has been done with family, my ex, or through my old job. In other words, I’ve just never had a romance abroad – at least not the kind that would inspire a 1980’s Taster’s Choice commercial.

(Anyone who grew up in the 80’s remembers Jean-Luc)

I explained to her, “I’ve never slept with a foreigner. Kissed, flirted with – yes. Sex, no. Well, unless you count The Russian.”

“I feel like there’s a good story here, Simone.”

I then proceeded to tell her exactly what I’m about to tell you.

I met the Russian on my first trip back to Toronto after I left in 2011. The Russian wasn’t actually Russian per se. He was from another former Soviet country, close to where my ancestors are from and had been living in Canada for several years, working as an exec for a successful Canadian company.

I was out for drinks with one of my best friends in Toronto at a bustling restaurant-bar in the Financial District. We hadn’t seen each other since I had left for the West Coast, however it only took a  few minutes and a vodka martini (or three) before we were chatting up a storm like not a day had passed. Although the friend I was with that night very much a savvy, whip-smart, self-made woman, she has a tendency to attract, date and socialize with wealthy, high-roller types. She’s also one of the most fearless and confident people I know. So, I wasn’t surprised when an older, moneyed guy and his younger, noticeably attractive friend stopped by our table to say hi.

“Simone, this is ____ (older guy), he’s the CEO of _________ (insert well known Canadian company) and he dated ________(our friend)”

Then, she introduced The Russian.

“Simone, this is ______ (typical Russian name). He’s originally from ________ (insert former-Soviet country.) Typical Russian Name, Simone’s relatives are originally from your country. You guys should talk” she said with a wink.

She didn’t miss a beat before suggesting that the guys buy us a couple of rounds of drinks.

There was no doubt that The Russian was very handsome. He looked like a younger, better looking Mikhail Baryshnikov (my very first celebrity crush): sandy blonde hair, square jaw and blue almond shaped eyes that radiated just the right amount of mischief and sex appeal. Like many of the men on my Mom’s side of the family, he was built like a reverse triangle: broad shoulders, lean and muscular.

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Later, when I showed a photo of The Russian to my best-friend, she commented, “He looks like the kind of guy you’d meet on an Olympic podium, not in real life.” She wasn’t far off.

So, when the guys asked us if we’d like to accompany them to their next location, it was a no brainer. A few minutes later we were all hanging out at a very swanky hotel bar known for being a popular hangout for investment banker types, celebrities and high-end escorts alike.

While my friend chatted with CEO guy, The Russian and I were huddled close together at the bar, our legs touching. Although my friend has dated quite a few Russian and Ukrainian guys over the years, I explained that I had never really dated anyone who shared this part of my cultural background.

“Why not?” he asked.

“I don’t know. I guess I don’t know that many Russian, Ukrainian or Polish people outside of my own family. The guys that I have met, always tell me I look like I could be their sister.”

(This is true. My friend’s Ukrainian ex and I look like we could easily be related.)

“You’re beautiful. Not anything like sister to me.” he replied with a wink.

A few hours and quite a few vodkas later, The Russian suggested we all head back to his condo and continue the party there. Back at his place – a sparsely furnished, slick condo on the waterfront; my friend and CEO Guy talked business while The Russian and I vigorously made out in the kitchen. It had been months upon months since I’d had any physical contact from the opposite sex and let’s face it – he was hot. Although the free-flowing vodka definitely didn’t hurt, it wasn’t just the alcohol that was making me feel intoxicated, it was the Russian – the way he smelled (like freshly washed laundry), the feeling of my hands running through his hair, his lilting accent as he whispered in my ear that he thought I was sexy. We had chemistry. This much was clear.

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“I’ve never seen you like this!” my friend told me, once I’d been able to pry myself from The Russian’s lips long enough to come up for air.

“You mean single?”

“Well, yeah…and like, clearly ready to mingle!” she replied with a raised eye-brow.

It’s true, this is one of the first times we’d hung out since my big break-up a few months before and the first time she’d ever seen me with my arms wrapped around anyone other than my ex.

When things in the kitchen started to get particularly heated, the Russian and I moved our make-out session into his bedroom where we quickly became a tangle of naked limbs atop of his bed. He tore off my panties and proceeded to go down on me with such precision and vigour that it wasn’t long before I lost my breath as my back was arched in pleasure.

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On Life, Love and Concerts

Years ago, I dated a guy who did not share my acute love for live music. When I admitted to him that I once once dropped $150 to see one of our favourite artists live, he responded by saying:

Why would you bother spending the money when you can buy the CD at Walmart for $10? That’s what I did.”

He just didn’t get it. Some people don’t.

Music is an important part of my life. When I’m not  researching new artists in search of the next great piece of ear-candy, I’m making plans to see my favourite artists live. Amazing life experiences are fleeting and you have to grab them while you can. This is why I spent most of my twenties, scrimping, saving and eating a lot of instant noodles so I would be able to see most of my favourite artists live. Even as a 30-something, I still consider going to see live music money well spent.

A good friend of mine is currently working on launching a new mobile music app called Syzzle. If you’re the kind of person who would rather eat ramen for a week than miss out on seeing your favourite band, Syzzle is the app just for you. With Syzzle you can rate live music, follow artists worldwide, receive tour alerts, buy tickets, locate the best music venues in town and a whole lot more. In other words, it’s like Yelp for music.

Remember that time you thought it would be so ironic to go see Hootie and the Blowfish live and when you arrived at the venue, you found out you’d actually purchased tickets to Hootie and the BlowPhish, a bizarre cover band that was really just a Darius Rucker lookalike in a rainbow dashiki singing acoustic versions of “Down with Disease”? Yes, that. Syzzle could have saved you from this atrocity. Instead, it’s likely you’ll never live this down.

Not all concerts can be earth shaking awesome, however the ones that are, have the potential to be transformative experiences. Whether it’s a lesson about life and love, or a broadening of my musical horizons, my favourite concerts are always the ones that have taught me something about myself. Since Syzzle is launching today, I thought I’d take today’s post as an opportunity to reflect on some of the things I have learned from my concert experiences.

I caught the concert bug after seeing one of my favourite artists, Erykah Badu, live for the first time in 2001. I remember racing down to Massey Hall on the day of the concert and buying last minute tickets, which just happened to be in the second row. I was nervous to go to the concert alone, however I ended up meeting a couple from Buffalo, NY who took me under their wing. Together we sang along to each song, as Erykah’s much-more-powerful-in-real-life voice hypnotized us. I learned that you shouldn’t be afraid of doing the things you love, just because you’re worried about doing them alone. Music creates bonds. 

The Fall of 2002 was a rough one: my Grandma passed away, my boyfriend broke up with me and the ceiling of my apartment collapsed. I was heartbroken and it felt like life was literally crashing down around me. To cheer me up, my recent ex-boyfriend presented me with backstage passes to hear Remy Shand live. Say what you will about the Canadian one-hit-wonder, but that guy can sing. My ex was not a good boyfriend, but on that night he was a good friend. Sometimes the people who break your heart are the ones who know how to put it back together. 

Live music can move you in ways you never expected. Like, that I time I went to see Basement Jaxx and I was dancing so hard I actually wet my pants a tiny bit. The lesson here: Unless you’re willing to live with this secret shame, drinking multiple neon blue vodka coolers and jumping up and down, do not mix. 

During a bizarre phase my mid-twenties, I dragged my punk rock music loving then-boyfriend to see Mariah Carey in Toronto. When the songstress entered on stage wearing a gold bathing suit and more fake hair than an Eglinton West beauty shop, my boyfriend leaned over and said, “I just don’t get whatever this is…but I love you.” Loving someone means accepting their quirks – even if one of those quirks is a fondness for R&B Divas.

This is the same guy who, after discovering I’d had a epically terrible day at work, insisted on blowing off his coworkers who had front row tickets to the Gwen Stefani show that night. Instead, he scalped his ticket and purchased two nose bleed seats so we could both go to the concert. I would have done the same thing for him, which made me realize we were both in it for the long haul. Although it didn’t work out, we’re still really good friends.

I’ve learned that you should always pay attention to a band’s name. If the band is called “Audio Sleep” don’t expect a dance party. If a band is called “Deer Typewriter” it’s likely that plaid shirts, ironic t-shirts and horn-rimmed glasses are not only an acceptable wardrobe choice, they’re required. If the band is called “Jessie and the Rippers” you’re in for a real treat.

Although 2011 was a hard year, going to hear Prince play live at my hometown arena was a highlight. As glittering pieces of actual Purple Rain fell on my cheeks, I was more sure than ever of the magical, healing quality of music. I also learned that when it comes to Prince, it’s possible for me to completely and hopelessly attracted to a 55 year old man in glittery, high heel boots.

I’ve learned through my concert experiences that the best concerts are the ones with heart, energy and the ability to make you reflect on that very moment in time. Live music can be transformative, it can make you feel like you are part of something much larger than yourself, but most of all, a really great show is just so much fun.

So, when that guy asked me, “Why would you bother spending the money on a concert when you can buy the CD at Walmart?” I knew unequivocally, that he was not the right guy for me. 

What have you learned from your concert going experiences? Please share!

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