Dear 16 Year Old Jenn Jenn…

Jenn and the city jennandthecity
Dear 16 year old Jenn Jenn,

I’m writing you to let you know that no matter how hard life seems right now – it will get better. I know you are frustrated, and that you feel alone. You feel uncomfortable in your own skin and unsure of what the future holds…but believe me when I say it’ll all be worth it.

Those kids making fun of you for being so skinny and not wearing make-up, ignore them. Because soon enough you will grow into a beautiful, independent woman who will be so strong-willed that you won’t take that kind of crap from anyone anymore. You will know your worth, finally – and you won’t settle for anything less than you deserve.

Keep writing. Write down every thought and feeling that comes your way. Carry around a notepad because you will never know when inspiration will strike. It could be a sudden warm breeze that you feel through your hair on a summer evening that’ll inspire you to write about how free you feel, or it could be those late nights you spend lying in bed wide awake, mind racing, when you’ll be motivated to share your deepest secrets. These inspirational moments can strike at any time and you want to be prepared because that’s when the good stuff comes – when you least expect it.

Stay true to who you are. Don’t change your beliefs and your morals just to fit in. It’s ok to be different, it’s better that way. You see things, the world, in a different perspective. Keep that optimism and faith in humanity, because lord knows we need more of that.

When it comes to dating and relationships – slow down. Slow down, and before you even begin to think about allowing someone else to love you – love yourself.

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Stress Relievers – Take A Chill Pill, JJ

As you can probably guess from my Twitter, Instagram, Facebook, and Snapchat accounts – my life can get very busy. It can be hectic trying to juggle everything at once. From my full-time day job – to writing blog posts; from going to events – to going out on dates; from making the time to hang out with friends and family…it can all be a bit overwhelming and stressful when trying to coordinate everything.


Side Note: I am not complaining. At all.

I am very fortunate to be in the position I am in and have the ability to do the things that I get to do. Believe me, I know this. But what I have come to learn over the past couple of years is that sometimes you need to take some time for yourself. Take a step back and think about what makes you happy, genuinely, to your core…and do more of that.

So what do I like to do to de-stress when life gets so crazy?
Rub A Dub Dub – Get In The Tub

There is something about filling up your tub with bubbles and/or bath bomb and just soaking away your stress. Seeing as I live alone, I leave my bathroom door open and my dog and cat often come in and lay beside the tub…those darn pervs, watching me take a bubble bath! I usually zone out and get lost in the latest season of Playing House on shomi or bury my nose deep into my latest book. By the time the water has turned cold and I’m all pruney – I get out and feel so much more relaxed than I did prior to hopping in the tub.

Run Jen(ny), Run

music on, the world off – running is my therapy

A photo posted by Jenn and the City (@thejennandthecity) on

Running is my therapy. I have a love-hate relationship with it, but running is seriously one of the things that keeps me sane. I love waking up bright and early, lacing up my fave kicks, and just running. I don’t always plan a route and to be honest, I don’t even always bring my phone. There’s something almost zen-like about being out there alone, running and hearing my feet hit the pavement.

Just never, ever call me Jenny. K? Thanks.

They Say Laughter Is The Best Medicine

jenn and the city toronto skyline stress RelieverI’m out so often for the blog that on the off-chance I do have a night without any work plans, one of my most favourite things to do is to spend some one-on-one time with someone who makes me laugh. We’ll open a bottle of wine and just let the conversation flow. No need to go out to a local hot-spot, no need to get all dolled up – just spending that quality time together is more than enough. And sometimes a view like that one above is part of the package…which isn’t too shabby if you ask me!

Sports, Go Sports

Rogers 4K Blue Jays #LifeIn4K stress Reliever

Ok, I often make the “Go Sports!” joke on Twitter, but the truth of the matter is I am actually a sports fan. While I may not be a “die-hard, be at the ball park or arena every week, know every single stat fan” – I do enjoy watching multiple sporting practices. Shocker, I know. So, as part of the #RogersSI team – when Rogers and Samsung reached out to partner for the launch of 4K streaming of the Blue Jays season – I was excited. Throw in the 55″ 4K TV from Samsung and Rogers’ NextBox 4K Cable Box and I was all set up to catch all of the Blue Jays games on from the comfort of my own home – and I was ecstatic! Having my family or friends over to watch a game is a great way to de-stress. My nieces are becoming baseball fans in their own right, so to have them over to watch the game(s) is a way to build these traditions and memories that will stay with us for years to come. We get to experience #LifeIn4K, “TV like never before with resolution that’s 4 times better than HD alone; with sharper images and realistic picture quality, everything you watch comes to life,” from the comfort of my own home. Really, what more could a gal ask for?

What are some of the ways you like to de-stress when life just gets to be too much and you literally can’t even?

Hit me up on Snapchat and show me!

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Chapter 7 of 12 – Bring On The Sunshine

jenn and the city

Oh, hi guys! It’s been a minute since I checked in with y’all.

How you dooooin?

Life has been a bit hectic on my end and I’ve been left feeling like I am constantly playing catch-up. Couple that with my anxiety and it’s a recipe for trouble. #welp 

But I’m here, and I’m happier than I have been in a long time – and I feel like I’m getting back to myself…and my old ways. 😉

views from #the6ix

A photo posted by Jenn and the City (@thejennandthecity) on

So much has been going on, both in the #bloggerlife and personal aspects of my life. Truthfully – I kind of just needed a little time to pull myself back from being online as much and spend that time and energy elsewhere. Be it through my early morning solo runs that I consider my therapy, or spending some time with friends (both new and old alike) and family – I just needed some ME time. 

But – don’t you fret. I’m back, babes!

I have some GREAT stuff I’m going to be sharing with you over the next little while. I’m going to give you a behind-the-scenes look at some of the events I’ve gotten to attend lately, and I have some killer recipes (both food and cocktail, because why the heck not) that I’m going to be sharing. I’ve partnered with some awesome brands and can’t wait to share all of that with you. 

I’m still continuing on my fitness journey and want to share that with you guys as well. I’ve had my ups and downs, some minor setbacks – but that’s life. Life happens and you have to find a way to power through and just do you. You know what I mean? There are no more excuses to be made. It’s all about living your happiest and healthiest life, however works for you.

And, of course, I’ll be writing more personal posts about life and love and everything in between. Sharing my stories has been therapeutic for me, and to top it off – getting such overwhelming responses from you guys through Twitter or Facebook messages and emails makes my heart so happy! 

Now I’m off to enjoy the long weekend and I hope you are too!
Sending all the positive vibes and sunshine your way.

jenn and the city

Letting Go And Starting Over After A Break-Up

After a break-up, nothing in the universe can stop you from letting go and starting over.


I’m the type of person who goes all-in. I give my all, my whole heart – loving unconditionally and fully. Jumping in without worry of consequences. Then, when things don’t work out as I had hoped – I’m left questioning myself, my worth – wondering what it was that I could have done differently. What is it that either of us could have done differently? But, it’s just not that simple. It’s never just that one thing that could have changed.

Sometimes, no matter how badly you want something to work out – it just isn’t right.

Life happens. Things happen – and you may not ever know exactly where things went wrong – but the fact of the matter is that they did, and you have to move on.

So then what do you do? I mean, besides spend a weekend surrounded by friends and family, and lots of wine – of course.


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You Deserve The Best – So Stop Settling For Anything Less

dating and relationship advice

So often, single friends and acquaintances have come to me and asked me,

Why can’t I find someone?!” or, “Why am I still single?!

My first piece of advice is to cut out those “sort-of” relationships in your life.

By allowing those “sort-of” relationships to hold a place in your mind and in your heart – you are blocking out a space that could be otherwise occupied by something more worthwhile, more deserving.

It can be scary being utterly and completely alone. Trust me, I know this.

So you hold onto those “sort-of” relationships, thinking it’s better than nothing.

But believe me – it’s not.

Let go of the past, the what-if’s, and the sort-of‘s which are all poor excuses for relationships – and make room in your heart for the real deal…then you’ll be truly ready and it’ll come.

You’ve Laughed At My Suffering – Why Not Learn From It Too


UPDATE: I’m back on the market. ¯\_(ツ)_/¯

In case you’ve been living under a rock for the past month or so, you’ll know that your girl JennJenn over here is officially off the market. Yup, that’s right – I’m a spoken for gal now.


That being said – I know that over the past year you guys have thoroughly enjoyed reading about my torturous first dates, but don’t fret – I think I’ve found a great solution. I’m going to share with you some tips that I’ve learned from a year of first (and second, third, and sometimes even more) dates.

Dating doesn’t have to be difficult.

You’ve already laughed at my suffering, why not learn some tips from it too? LOL

1. Math is hard, but chemistry is even harder.

Chemistry is one of those things you either have, or you don’t. While you’re swiping left and right on your preferred online dating app, you may come across a picture or profile that catches your eye. You may even exchange some witty banter and clever conversation back and forth – but if and when you meet, and that chemistry isn’t there, know that it’s is something you can’t force or manipulate. Sure, it may not happen right off the bat on the first date (nerves and all) – but, know when to hold them and know when to chuck them the deuces. There is no point in wasting your time on something that just isn’t right.

2. It’s not always indigestion – trust your gut.

Don’t settle. I repeat – DO NOT SETTLE. Just, don’t. I know it can get lonely, I know it can get frustrating. Trust me – I KNOW. But for the love of everything holy – just do not settle. There were times I went out on a first date with a guy, and while it was all find and dandy…something just felt ~*off*~  Then I’d go on a second, or third – and that ~*off*~ feeling was still there, yet I’d pursue it in the hopes that something would change. Surprise surprise – it never did. Trust your instincts, that women’s intuition (or whatever the heck the male equivalent is)…when it’s just not right – walk away.

3. Don’t get swept up in the numbers game.

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#FitnessFriday | Here We Go…Again

Copy of #DublinItUp

It’s 7am on Friday morning and I’m still laying in bed. I should have gotten up a half an hour ago when my alarm went off and I was jolted out of my peaceful sleep. It was one of those sleeps where you’re in the sweet spot on your bed, curled up perfectly enjoying a lovely dream-filled sleep. But alas, the dreaded alarm came and awoke me. Truthfully, the alarm itself isn’t so bad (Drunk in Love remix with Kanye West – LOVE it) – it’s more the gEtTiNg Up part that sucks. Not to mention I can barely feel my legs. And before you ask – no, I wasn’t hit by an 18-wheeler – but I sure do feel like I had been.

Nope, I’ve just been working on my fitness.


I have shared some of my attempts at getting back into shape here on le blogaroo, and while those attempts were great at the start…let’s face it – they were half-assed. I was the first one to make excuses.

“Oh, I can’t go to the gym today – I have XYZ event tonight…there is just no time!”

“Oh, no no – I can’t workout today, I, ummm, I have cramps. Yeah. That’s right – cramps”

“Sorry. Can’t go to the gym tonight. Just don’t want to.”

Welp. Stop judging me, guys. At least I can admit when I’ve messed up! Anyways…moving on.

Things are different now though. They are, seriously. It’s not so much about specific goals, like – I don’t have a goal weight in mind, or a date that I want to lose x-amount of weight by. This time around I am making healthy changes in my everyday life to live a healthier life overall, and be the best version of me…right now, and long-term.


So, what changes am I making exactly, you ask? Well – I’m glad you asked, my friend! They are some pretty easy and simple changes that literally ANYONE can make. I live a crazy busy and hectic life. I feel as though I’m always on the go and playing catch-up – but that being said, I have come to the realization that these changes (and more – stay tuned for those) NEED to be made. I’m only one person, here for one lifetime – so I should be doing whatever I can to ensure a) that said lifetime lasts as long as possible, and b) I have a kick-ass time while living it. LOL

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There Are No Shortcuts In Life – Let The Universe Work Her Magic

Let The Universe Work Her Magic

Love it or hate it, Sex and the City often provided some sound advice when it came to life and love. Over the past year and a bit, my year of singleness, (singledom?) – I found myself re-watching old episodes more than I care to admit. When I was having a rough day, sometimes the only thing that got me through it was the thought that at the end of the day I’d be curled up on my couch, with an open bottle of wine, watching as Carrie, Miranda, Charlotte, and Samantha attempted to maneuver their way through dating in New York. Every so often I’d mumble under my breath, “I am so a *insert SATC character name here*” as I grabbed another slice of pizza. It’s what the single ladies do, right?

in love with my pizza

No? Just me? Awks. Moving on.

There is one piece of advice that really hit home for me, though. It’s something I’ve heard so many times, but it never sunk in. Don’t you hate when that happens? You hear something, and you know it’s true. In fact – you know it’s so true that you share that advice with others…yet, you don’t follow it yourself. Ugh. Worst. Anyways, shortly into my year of singleness – I heard this advice again while stuffing my face with pizza and watching SATC, and it was as if it was JUST the wakeup call I needed.

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Skip The First Date Interview – These Questions Will Actually Create Conversation

first date advice

I have so many friends coming to me and asking for my advice when it comes to online dating. They’re out there, playing the field – but are having no luck when it comes to a) finding quality matches, and b) securing dates. Seeing as I have been on my fair share of dates over the past year, I know that things can become repetitive, boring even. Whether it’s in the conversations leading up to your date, or even on your first date – it often feels as though you’re on a never-ending interview, answering the same general questions.

Where are you from? How was your weekend? Etc., etc. 

BORING…and for the most part, not relevant. Chances are in your online dating profile – you answer many of these mundane questions. If you’re looking for love through online dating – it’s time to start digging a little deeper and getting to the good stuff. You need to see if your personalities mesh well, and you can do this by asking great questions and learning more about each other on your first date. By the end of your first date you want to see if you connect with this person, whether you share similar values, and figure out if this is something you want to see flourish. By asking the right questions, you can determine if this is someone you want to learn even more about.

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When Did Games Get So Difficult To Maneuver And Less Fun To Play?

dating games

When we were kids, all we wanted to do was play games. Hopscotch, tag, duck-duck goose – whatever the game was, we were down to play it. Now that we are older, we’re faced with a different type of game – the dating game. Subsequently, within this game there are even more games.

So, that begs the question – when did things get so complicated? I mean, isn’t dating is supposed to be fun? Isn’t it supposed to be exciting? When did the game(s) get so difficult to maneuver and less fun to play? These games, the waiting 3 days to return a text even though we are all within arms reach of our phones at all times; the keeping your options open, just in case; the pretending to be someone you’re not simply out of fear of ending up alone – they’re so silly.

I say throw caution to the wind and enjoy the ride. If you like someone – tell them. If you don’t – tell them that too. Don’t pull a ghosting act and just disappear – show some respect (and be a decent human being) and just be honest. Backstreet Boys said it best, “Quit Playing Games With My Heartlolz.

Speaking of the games – what happened to the days where when you met someone new and things were just effortless? Your conversations flow, and they literally only end because sleep must come at some point. Building that connection where you hang off of every word they say, when you want to know every little thing about them?

But really, shouldn’t that be how it actually goes?

When something like that comes into your life, it can catch you off guard. (Trust me – I know) It’s a new, weird, odd feeling. We’ve grown so accustomed to the games that when we meet someone who isn’t playing them – we’re left wondering why? How did this happen?

Maybe the way we should go about it is by not questioning why, or how. But instead we should be embracing it. Sometimes you find exactly what you’ve been looking for, when you stop looking. You have to take a step back and put your faith into the universe. Have faith that when the timing is right, things will align.

Maybe when that new person comes into your life, leaving the games at the door – that new, weird, odd feeling is actually what you should have been feeling all along. It just feels right, effortless. As opposed to the constant stress and worry, you’re now in a state of excitement and eagerness to see this new thing through. When you see their name pop up on your phone screen your heart flutters because it makes you feel so amazing that for even jus that moment in time – you crossed their mind.

Put your faith in the universe and let her do it’s thing. Trust me, because when timing and chemistry align, beautiful things can happen.