Things You Will Learn From Dating a Younger Man

On July 1st you receive an email from your ex in Toronto – the one you left behind when you moved back to the West Coast – letting you know that he’s met someone and in a few months he will be a father.

The news throws you – not because you aren’t happy for him – you are (he will be a kick-ass dad) – but because this is his dream. The dream he wanted for the two of you. The dream that you couldn’t deliver on for him.

Clutching your smartphone, you break down in tears in the garden section of Capital Iron, while your Mom strokes your back and asks you what’s wrong.

You haven’t lived in Toronto in nearly three years, however you cry because in this moment it feels like the life that you used to have there really is over. Although the future is exciting and exhilarating, it’s also kind of fucking scary.

The future is happening right now.

Although you feel slightly untethered, you decide to slap on some make-up, put on that new dress and go to a Canada Day BBQ that you’ve been invited to.

Dating a Younger Man
Your friends pick you up in a 1950’s mustang convertible. Disclosure is playing on the stereo. Driving along the beach as the warm air rushes past you, life feels oddly perfect.

At the BBQ is where you meet him. You notice him right away because he has what some people might call “swagger.” He’s tall and athletic looking with a strawberry blonde Macklemore haircut. Acne scars faintly dot his chin.

You hear him talking to some other people about Toronto, at which point you join in on the conversation. It turns out that he used to live there, on the same street as you – just a few houses down from the gorgeous brownstone that you used to share with your ex. What are the odds? This must be kismet.

You’re on your third hot dog of the evening. He’s eating ribs. When you notice him scrambling with his hands full to pick up another beer, you politely offer assistance.

“Would you like me to hold your bone?” you ask.

“Yes, please” he replies.

You talk some more. You laugh. He comes with your friends to watch the fireworks from a cliff overlooking the ocean.

It’s only later that you learn that he’s six years younger than you and went to junior high school with your baby sister.

A few nights later you go for drinks at a chic wine bar. He insists on ordering a nice bottle of wine to share and picking up the cheque. You’re impressed.

You laugh. You kiss. You have sex. You wake up wrapped in his sinewy tanned arms and think,

“I could get used to this”

By midsummer you’ll change your mind and you will no longer be dating. However, before that happens you’ll learn a few things along the way.

You’ve never dated a younger guy before. After attempting to date a variety of divorcees and single dads, you’ll find this guy’s total lack of relationship baggage utterly refreshing. However, you’ll soon realize that the flip side of this is that he seems to have no serious relationship experience whatsoever. This starts to reveal itself quickly.

Dating someone younger often means that their exes are young too. When you stumble across a photo of his ex-girlfriend on Facebook, you discover that she looks like a younger, firmer, more proportional Kim Kardashian. It gets worse when he tells you that they broke up six months ago – right before her 19th birthday. Now, you know you look good for a 30-something, however when you don’t hear from him for a few days you start to wonder if maybe he finally noticed the fine creases on the corner of your eyes and promptly got freaked out.

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On Dating, Chemistry and Rejection

Disclaimer: none of these gorgeous photos were taken by me. All have been found via One Sixth Avenue, Black Mountain Prophet &Steven Henke.

Lately, I’ve been spending a lot of time pondering love, dating and rejection.

Why? Because if you’ve dated more than one person, most likely you’ve been rejected.

Think back to the first time someone broke your heart. For me, it was the summer after high school. I was dating a guy who has since become known as “Dave the Rollerblader.” Dave was your typical happy go-lucky beach bum with an affinity for tanning, taking photos of himself with his shirt off and long rollerblading sessions along the beach. We’d spend long, warm summer evenings making out in the front seat of his pick-up truck. We had nothing in common, and yet I fell head over rollerblades for him. When he broke up with me because he was moving to Australia to surf full time, my heart was broken. I stayed in my bedroom for a whole weekend listening to Boyz II Men’s “End of the Road” while bawling my eyes out. To say I didn’t handle this initial rejection well would be the understatement of the century. Then again, I was 18 years old, experiencing heartbreak for the first time. Can you really blame me?

rejection 7
If you read the story about my romance with rollerblading Dave, you’ll understand what I do now: that by breaking up with me he did me a huge favour. Our short-lived  relationship and it’s eventual demise now seems laughable, however at the time it was absolutely crushing. That’s because when I was in my teens and early twenties I lived in a perpetual state of fear when it came to rejection. I’d meet someone I really liked, start dating them and then spend the entire relationship worrying about when they would break up with me. I was guarded, I was a little paranoid and I tried way to hard to hang on to people that I should have just let walk away. In turn, my fear of rejection became a self-fullfilling prophecy of sorts. When things eventually did fall apart (as they inevitably would) the break-up would seem completely debilitating. {photo via Steven Henke}

I read a quote recently that went something like this: “Everyone you date, you’ll eventually break up with or end up marrying.” Although a lot of couples do stay together forever without a legally binding agreement, it’s still a sobering thought. {photo via One Sixth Avenue}

Rejection sucks and sometimes it really, really hurts. However, as much as we try and deny it, it’s an inevitable by-product of dating. How are we supposed to find the right person if we never reject or get rejected by the ones that aren’t right for us?

I have a lot of experience being rejected, to the point where I now consider myself a veritable rejection expert. However, now that I’m single and dating in my 30’s, I’ve decided to take a more positive approach to rejection – both as the rejector and the rejectee.

Here’s a few things I’ve learned about rejection that I wish someone had told me when I was younger.

rejection 1
1) It’s not about you – I used to take every rejection, every ghosting, every unreturned text message as a personal assault on my character. However, I’ve since learned that often getting rejected has very little to do with you. If someone chooses to not ask you out on another date or continue a romantic relationship with you – that’s their choice. They were choosing what was best for their life situation. For example, I’ve met tons of guys who I thought were truly fantastic, however we just didn’t have any chemistry. I imagine there have been many guys who have felt the same way about me. {photo via One Sixth Avenue}

Furthermore, if someone chooses to reject you in a really immature manner – for example, by literally disappearing off the face of the earth with no explanation, being lame about returning your texts or standing you up on a date, that’s on them. I read a quote somewhere that went something like this: “It’s not our responsibility to try and understand why people have the shortcomings they do, but to accept them & move on.”

rejection 2
2) Chemistry is ridiculously important – Like I mentioned above, I’ve met some truly fantastic dudes since moving back to BC, however kissing them feels like kissing a brother. There’s no big fireworks. It’s just…well, neutral.

Chemistry is a mysterious, biological force that acts on a subconscious level. Dating is like a science experiment: you combine different chemicals and hope for a reaction, but sometimes it just doesn’t happen – and you know what? That’s OK.

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Things You’ll Learn About Love & Sex at 33

When it comes to love and sex, being 33 is both totally weird and awesome.

On one hand, your hormones are raging and you want to have as much sex as possible. However, after a decade of bad decisions in your 20′s you’re now way more selective about who you sleep with…well, sort of. Most days you want to have sex with everyone and no one all at all the same time.

You’ll tell yourself that marriage isn’t really on your mind, but that it would be nice to meet someone that you could actually settle down with. However, some days you’ll catch yourself saying stuff like,  “At this point I don’t even care about finding ONE, I’d be happy to meet someone who is nice and reasonably normal that I can have regular, good, sex with.”

(gorgeous photo found via Keiko Lynn)

Your Pinterest account reveals your true feelings though. Amongst boards devoted to home decor, lingerie and whimsical vintage imagery, lurks one called “Creepy Imaginary Wedding” where you pin to your hearts content all things nuptial related. For someone who is always saying she isn’t even sure whether she believes in marriage, you sure do know what you want. (FYI, you’re thinking a classic, old school Hollywood vibe, bright fuchsia flower arrangments, a modern multi-cultural menu, somewhere like the Ace Hotel in Palm Springs. It will be hip and quirky, but still very classic and you’ll wear something Reem Accra or Elie Saab -ish obviously. Your groom will look elegant and handsome and won’t be wearing wrap-around sunglasses)

You spend more time than you’d like to admit wondering what your future dates will find more off-putting: The Creepy Imaginary Wedding, your professional relationship with Joe the Intern or the fact that you write about your vagina on the internet. You decide to stop worrying about it and instead just own it. After all, someone who doesn’t accept you for who you really are isn’t worth your time.

You’ll have good sex, “Okay-ish” sex and sex that is so bad it’s comical. More often than not you’ll have sex with yourself. You’ll come to the conclusion that you can go without sex for a long time, however going without an orgasm is another story. Your collection of sex toys will grow exponentially to the point where you start to run into storage issues.

When you get the urge for actual human contact, you’ll date people.

You’ll meet a 40-something single dad, whom your attraction to defies logic. However, when you go to have sex, you’ll be reminded that some people will use ridiculous excuses to get out of using condoms. He’ll insist that instead of using a condom, you should “just trust him.” This will also remind you of something you learned in your 20’s: that anyone who uses the line “just trust me!” should absolutely not be trusted. Later you watch an episode of Portlandia and determine that this guy must liken himself to be some sort of “pull out king” – albeit, a rather unsuccessful one: he has three kids.

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10 Things I’ve Learned About Love From “How I Met Your Mother”

A modified version of this post originally appeared on We Love Dates.

It’s no secret that I love How I Met Your Mother – in fact, rarely a day has gone by over the past 9 years when I haven’t quoted or referred to the show in conversation. Yes, I’m that friend. Trust me, between that and my 30 Rock references, it drives most people crazy. With only one final episode left before we say farewell to the show on March 31st, I’ve already begun preparing myself (as I’m sure many of you have) for major withdrawal symptoms. In fact, I have the second to last episode loaded on my computer ready to watch but I can’t yet because, well, it’s the second to last episode. Although I’m excited to see how everything wraps up, I’m not ready to say goodbye to this show. I probably never will be. There’s just so much about life, love and friendship that HIMYM just gets.

So, before we say goodbye and use ALL THE TISSUES in the world, here are a few of my favourite lessons about life & love from Ted, Robin, Lily, Marshall, Barney & the gang.

1. Too much compromise is never a good thing – Every relationship requires some level of compromise, after all,  a couple can’t work if they both had a personal mandate of “my way or the highway.” Being part of a relationship means working together. However, when you expect your partner to go to great lengths just to please you – for example, when Barney asked Quinn to quit her job, or Victoria asked Ted to stop being friends with Robin – it essentially means you want them to be someone they’re not. A relationship shouldn’t require you to give up things that are important to you. If it does, it means you’re in the wrong relationship.

2. Trust is Key – In order for a relationship to be successful you need to trust each other completely. Lack of trust is essentially is what undid the pairing of Quinn and Barney. However, when it comes to Lily and Marshall – the fact that they are willing to share everything and anything with each other (even bathroom habits) – keeps them in sync and connected.

3. Even “perfect” couples fight sometimes – Although Lily and Marshall are basically one of the most perfect couples ever, they don’t always see eye to eye. They fight. They make up. They do it again. Being in love doesn’t mean being “perfect.” If you’re afraid to have arguments, everything will just build up to the point where it’s unhealthy, resentment breeds or things become completely explosive. The fact that most of the couples on the show are shown having arguments on a fairly regular basis reminds us that like them, we’re all just humans trying to do our best.

4. Re-visiting exes usually doesn’t end well – Failure to follow this advice may find you on a date with your balding high-school ex-boyfriend from Canada who still works at a water-slide park, or getting kicked in the face in middle of a restaurant. Tread wisely my friends.

5. Love means accepting someone’s quirks – Whether it’s your best friend or the person you end up marrying, loving someone unconditionally means accepting their quirks, even if one of those quirks is a pair of bright red cowboy boots that they insist they’re “totally pulling off. ”

6. Sometimes your friends know you better than you know yourself – This is especially true when it comes to the people you date. When it comes to Ted’s love life, often the gang can spot things are amiss before he does – for example, when he gets back together with his painstakingly pretentious ex from college, Karen. Love is blind and sometimes we only see what we want to see. This is why you should always keep your good friends close. They want what’s best for you, whether you can see it at the time or not.

7. The “crazy eyes” are totally real – Listening to your intuition is an important part of dating. Often it’s our gut that gives us the best dating advice. If you look into your date’s eyes and feel uneasy, or your friends tell you that this new person you’re hanging out with gives them really bad vibes, take a moment to consider that the Universe may be trying to tell you something – i.e. that you should stay far, far away from this person.

8. You never know who you’ll end up with – [Spoiler Alert] At the beginning of Season One we never would have guessed that Robin would end up with Barney, but it happened. In fact, at various points throughout the show, several characters (including Ted himself) thought that Ted and Robin were destined to be together (even though as viewers we knew she was not The Mother.) I can’t tell you how many times this has played out in my life or the lives of my friends. Take a look at a summary of my sexual history – I thought a lot of these guys were “the one” at various points, however I am so glad that things never worked out with any of them. Same goes for friends of mine. Friends that I thought had “perfect relationships” have since split and moved on to new partners that are much better matches. This just goes to show that you can’t predict love. That womanizing, suit-obsessed guy that you currently don’t take seriously may just be the love of your life…or not.

9. Letting go is hard, but necessary – Throughout the series Ted struggles to let go of the feelings he has for Robin, to the point where it actually screws up several of his relationships. It’s only when he finally finds the courage to let Robin go that he opens himself up to finding true love. Coincidence? I think not. Sometimes we need to let go of good things to make room for amazing, awesome things.

10. Sometimes it takes a really, really long time to find the right person – If Ted’s 9-year long narrative has taught us anything, it’s that the path to true love is a long and winding road full of joy, heartache & lots of twisty turns. There’s someone for everyone and if you don’t give up faith, you will eventually find them. In the mean time, you’ll get by with a little help from your friends…

Greetings From The Bro-Zone

A few weeks ago, when I found out the guy I was interested in was seeing someone, I told one of my friends about the situation.

“So, he just casually slipped it into the conversation that he was dating someone, like out of the blue?!”

I was about to reply when it hit me –

“Yes, it was like he was telling his Bro or something. OMG, HE THINKS I’M HIS BRO. I’m in the Bro-Zone!”

I’m no stranger to the Bro-Zone. I’ve been in and out of the “zone” so many times over the past decade I’ve lost count.

Years ago, when I had just moved to Toronto started dating my first Toronto boyfriend, we went out for brunch with two of his best friends. We were still in the honeymoon stage and I remember my ex telling his buddies,

“Isn’t Simone great?!”

To which one of his buddies replied, “Yeah! You know who you remind me of Simone? You’re like the real life version of Janeane Garofalo’s character on Seinfeld. She’s funny, smart and sarcastic but when Jerry tries to date her he can’t because she reminds him too much of himself”

“Yeah, I mean you’re totally attractive but I’d never want to sleep you. You’re like, one of the guys. You’re too smart and cool to actually have sex with.”

The disturbing part was that I watched as my ex-boyfriend nodded in approval.

Ok, so being compared to Janeane Garofalo isn’t the worst thing ever (because, hello, she’s awesome) and I get that it’s totally not cool to tell your buddy, “Hey, I want to bang your girlfriend!” – but, was the last part really necessary?!

(For those of you who don’t “Speak Seinfeld” please see below)

This wasn’t the last time that I would unexpectedly find myself in what I’ve come to call the Bro-Zone. The ex I mentioned above would eventually decide that he wanted to be in the Bro-Zone all the time…and preferably naked. He bid farewell to vagina and our relationship when he broke things off a year later to date a guy he had met while working on a production of “Guys and Dolls.” File that under, “World’s Biggest Cliches.”

About a year after we split, I had a falling out with two of my closest female friends at that time. My partying had reached the point of self-destruction and both falling outs were the result of some pretty terrible decisions on my part. Although I knew my behaviour was at fault, the end of these friendships made me sad. I was carrying around so much guilt and hurt that for the next few years I was almost afraid to make new female friends out of fear that I might fuck those friendships up too. Instead, I focused on being friends with guys.

I love having male friends. Guys tend to be pretty straightforward and as long as you don’t sleep together (and even sometimes when you do), there’s considerably less drama than what often comes hand in hand with many female friendships. Looking to escape my recent bout of girl-drama, I took comfort in my male friendships.

In the inner circle, there was my Gay BFFs – my friend Trevor, one of my closest friends from BC (and my former prom date) and my friend Chris who was also my next-door neighbour.  Between these two, there was always someone around to talk to (often bemoaning dating, or the lack thereof), cook dinner with, go to concerts with & to spend late nights watching sex and the city episodes with when we were too tired or broke to go out drinking. These guys were my rocks and I don’t think I would have made it through that period of my life without them.

At the time I worked at a store that sold beauty products. Through my male coworkers I met a whole other slew of “gay boyfriends.” When I wasn’t hanging out with Trevor or Chris, I was getting into drunken antics with these guys. Gender never played a part in my other friendships, however my Gay Boyfriends always made a point of letting me know I was one of the guys – or, as they liked to say “One of the girls!”

I also had my straight male friends. We’d drink beer together after class, talk about “chicks” and sometimes they would help me lift heavy furniture. I was intent on becoming the best pseudo-bro I could be. For awhile there I was like the Paul Rudd to their Seth Rogan, The Michael Cera to their Jonah Hill, the Bradley Cooper to the Wolf Pack – except, I had boobs.

This photo is just as awkward for me as it is for you. Photoshop is not my strong suit. 

Then, there were the guys I slept with. I’ll get to those guys in a minute…

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