Home » How To Get Ready For a Night Out as a 30-Something

How To Get Ready For a Night Out as a 30-Something

Last week, when the Universe sent me a sign that I’m likely headed towards a life of living alone with an extensive collection of cat figurines, I decided to take matters in my own hands. Within a few minutes of publishing my last blog post I was on my phone texting one of single friends to arrange a girls night out.

Although I still love a good night of drinks and dancing, getting ready for a night on the town as a 30-something is an entirely different operation than getting ready for a night out as an early 20-something. When I was in my early 20’s party prep usually involved getting drunk in the shower, putting on clothes & eating a piece of 3 day old pizza so I wouldn’t throw up later. Party prep as a 30-something involves considerably more pre-planning.

Game day – 

The key to a successful night out relies on establishing the perfect caffeine to power nap ratio. You want to have just enough caffeine in your system to feel human, but not enough that you feel too jittery to have a late afternoon power nap. Failure to power nap before heading out will likely result in your getting the nods at 11pm or worse, copious pre-game consumption of red bull. You’ve learned from your twenties that the latter never ends well.

You look in the mirror and realize that your roots are starting to look way more like Barrack Obama circa 2013 than 2009. There’s no way you can go out like this, which means you’re going to have a to schedule in a trip to the drugstore to buy hair dye.

However, be careful that you don’t linger at the mall and whatever you do don’t say yes to that second latte – you wouldn’t want to risk missing out on your precious nap time! You end up lingering at the mall anyways (“Oooh, free tea testing at David’s Tea!”) leaving you only a 2 hour window to eat, dye your hair and get ready. Colouring your hair under tight time constraints: what could possibly go wrong?!

Forgo nap time. Make coffee instead.

Nutrition – 

You’ve learned from an unfortunate incident in your twenties where you spent two hours throwing up in the washroom of Woody’s that eating before drinking is imperative. To ensure optimal stomach comfort you eat a healthy, protein rich meal with just enough carbs to make you feel full without making you feel sleepy. Now it’s time for the grooming portion of the evening!

Grooming – 

In effort to get the hair dye on your head in the most efficient way possible you manage to drop the applicator. The dye splatters everywhere. There’s purple goop on the counter, on the floor, on the ceiling, behind the toilet.

Purple? That doesn’t seem right.

20 minutes later: Your hair isn’t purple. However, in the haste of cleaning up the bathroom, you’ve also managed to get the dye all over yourself. Your arm now has this weird purplish black pattern that looks like a cross between a bruise and a prison tattoo gone wrong. If you keep your right arm glued to your body the whole night no one will notice. Yes, that will totally work.

Your beauty routine hasn’t changed that much since your early 20’s. However, as a 30-something you’ve developed an addiction to $50 YSL Concealer. When you worked in your cushy day job you wore it everyday, however now that you’re a freelance writer you dole out your YSL with the same discretion as Elaine Benes deciding whether a guy is “Sponge Worthy.” It’s time to bring out the big guns. You apply your YSL liberally and hope it’s worth it.

Wardrobe Selection – 

Your hair & make-up are done and you’re feeling pretty awesome. Now, comes the tricky part: deciding what to wear. As a woman of the world, you know exactly what to wear for a night out in Toronto, Las Vegas, or even Miami. However, when it comes what to wear to go out in Sleepytown you always draw a blank. You know that whatever you decide to wear, you’re likely going to be overdressed or look out of place. If you show up in jeans and heels, everyone will be in sweats. If you show up in a cocktail dress, everyone will be in jeans. If you show up in a Elie Tahari suit, everyone will be in skin-tight body-con dresses. You can’t win.

At 8:01 pm you decide to say “Fuck it!” and go for a look you call “downtown cool” – a white Alexander Wang silk blouse, a vintage Tibi mini-skirt & a Miu Miu clutch. At 8:01 pm you put the Alexander Wang blouse back in the closet after you have visions of someone spilling Jungle Juice all over you. At 8:02 the Tibi skirt also goes back in the closet when you remember what a bitch it is to dry clean.

 At 8:04 pm you settle on a $20 skater style, leopard print dress + your favourite pair of black stilettos and say a silent prayer that you don’t drop your favourite clutch on the bathroom floor.

Convinced that you’ve managed to come up with an outfit that’s the perfect mix of sexy and machine washable fabric, you step out of your bedroom to show your mom and sister.

Mom: “You’re wearing THAT?!

Sister: “Don’t you have any nice clothes to wear?”


Sister: “Maybe you should just stay home”

Me: “AHHHH!”

You storm back into your bedroom.

(The joke is on you. When you get to the bar to meet your friends you realize that everyone is wearing jeans, t-shirts and flat boots. Go figure.)

Personal Confidence – 

You’re in need of a serious confidence boost so you give yourself a pep-talk that sounds something like this –


The pep-talk actually works a little too well and you decide that now is the perfect time to take a few photos for your long-distance sexting buddy – after all, you’re wearing eye-liner for the first time in three weeks. You’re getting really into taking selfies of yourself in your new red lingerie set, when you realize you should’ve left your house 10 minutes ago.

(Some things haven’t changed since your 20’s, however this time you can’t blame it on the booze.)

Transportation – 

Normally you would just hop in a cab but there is no time to call one. Your friends are only three very long blocks away so you & your stilettos decide to make a run for it. You barrel down the street, heels clicking loudly on the pavement, desperately trying not to wipe out or crash into the group of hippies who have decided to smoke pot in the middle of the sidewalk. You arrive out of breath but are relieved to be greeted by the smiling face of your fellow single friend who gives you a big hug.


You do all of this so you can be followed around the bar all night by a Taylor Hicks look-a-like, who eventually corners you to discuss kayaking.

When the Taylor-a-like turns the conversation to life jackets, hiking and where to find the best tents in this city, you once again say a silent prayer  – this time for your girlfriends.

If it weren’t for them, you’d likely be running out of the bar as we speak.

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