Today is a special Friday for me because it's the anniversary of the day B and I first met. I know, whooooo celebrates the day they first met? Whooooo celebrates anniversaries when you're not even married?

To be honest, I never did before.

But there's something special about this one. Throughout most of my twenties I was single. I dated here and there, but I never really found anything 'special' and so i enjoyed the last five 6 years of my twenties sans ball and chain traveling around, partying my butt off and third wheeling with my friends at my own free will. And it was FANTASTIC! I can happily look back on my twenties and smile at all the amazing things I got to do as a single gal. But once I turned 30, I wanted to share my experiences with someone, but I wasn't really a bar start anymore and my social scene made it difficult to meet someone. So I did what any millennial would do, I secretly and almost shamefully resorted to Tinder. I followed the journey of swiping left and right and being taken out on dinner dates in Toronto, not answering matches messages because they're pick-up lines were so awful, making fun of shirtless gym and bathroom selfies with my fellow single mates who also had to turn to Tinder and the rollercoaster ride of the ups and downs of dating. After several months of swiping left and right and going on mediocre dates, I was at my wits end. My plan was to give it one more shot, and if it didn't work out I would save my money for one year and then take a year off to travel. I was actually excited about this plan, which is why I felt MEH when Bryon and I matched. Okay, he WAS cute, but he literally said hi, and because I didn't message him back soon enough (I WAS BUSY) he sent me a novel about himself. Like we're talking an essay all about his likes and dislikes and then ended it with I would really like to take you out for dinner.

Whoa bro, you don't even know me yet...but I love your tenacious ambition to get right to the point and ask me to dinner. So I finally responded and said sure.

But it didn't quite work out. He planned to take out and then realized he had a wedding that day. What followed was a series of drunk texts while he was at that wedding about how I wished I could wear scrubs to work too, and B saying, "Yea they're great because you can just wear them and walk around like you know what's going on" which alarmed me because he's a doctor. He also expressed his hatred for dentists in his drunken stupor, which made me laugh. We tried to work out another date, but I think I either didn't answer or I was just too busy to answer.

A couple days later he messaged me again. "Hey Caitlin, I'm gonna try this one more time. I would really like to take you for dinner, are you free at all this week?"

I really felt for the guy and for my wilting relationship status. He had been making me laugh this whole time, I felt like he might be as awkward as I am. He didn't have any shirtless selfies of him in the bathroom (a popular pose for guys on Tinder) or selfies in the gym so it would stupid if I didn't give him a chance. I told him I was free Thursday, and he told me to meet him at Her Father's Cider bar at whatever time he proposed. I'd like to say things ended there and that's when we started dating. But it doesn't...this is where things went wrong in the best way possible, and why I wanted to celebrate this day.

On the Thursday I wore a blue silk dress and a new pair of strappy heels. I curled my hair that morning. When I got outside the humidity was that of a tropical rainforest at its peak time of the season for hot weather. My hair fell flat and frizzy. I went about my day at work avoiding the outdoors so I could at least preserve my makeup. But when it came time to hop on the subway to meet him, the subway felt like a terrarium. And then as I was transferring subways, there was a massive delay, and there I was. Stuck underground where Toronto is literally its most hottest and humid. Seriously, ask any Toronto commuter. I was sweating through my silk dress, there were beads of sweat running down my face, I was late but had no cell service. It was a nightmare...on top of that, I was completely frazzled. When I did get off the subway, I realized I had a 15 minute walk to the restaurant (13 minutes into my walk I realized this) and Bryon thought I was a no-show.

I finally got there and when I greeted him I told him not to hug me because I was sweaty lol (I'm literally the most awkward person on dates...although I told him this in advance). I wore my sunglasses until the sweat was gone and tied my hair back. A storm was brewing and the wind gust knocked a patio umbrella out of its stand and it literally almost impaled B. A group of three overheard us discussing my peanut allergy, and for some reason I mentioned it was okay that he was a doctor...they were also doctors, and B had to clear it up that he wasn't MY doctor (this is frowned upon) and we were just on a date. The waiter brought out our food and described Bryon's elaborate dish and then set down my naked salad and said dismally, "aaaaaaannd, you have a peanut allergy". There was a lightening storm that moved us indoors, and then when it cleared we went back outside and by this time we were drunk. My pea-sized bladder made me get up to pee every five minutes. Bryon fell up the stairs on his way back the washroom (he told me). It was literally the most disastrous date ever, but....

He got into the Uber (who drove like a maniac) with me and said he would ride with me to the train station, which was out of his way. In the Uber he casually said, "so, when are you free again?"

I'll never forget walking into the restaurant and seeing B sitting there, one and half ciders in, looking nervous with his shirt buttoned all the way up. I literally took a breath and considered how I looked and thought that he would be the one that got away. But now, I can't imagine life without him.

So, in lieu of this special day, FriYay Affordables is all about date looks. I've created six awesome date looks for various occasions. So whether you're about to have the most disastrous date ever or you're celebrating 15 years as a couple, these will work out great. Each items in the outfits are under $100 USD

(aren't you happy to be getting a break from reading about the Nordstrom anniversary sale...)

Patio Dinner:

date night outfit


This is one of my favourite looks. The top is so fun and the white jeans really make it stand out! Nude strappy heels keep the eye drawn to the focal point of the outfit (the top) and the gold charm necklace just adds a dainty feature. I thought red lipstick would really accent the red in the top. The black bag blends with the top so the shirt can do the talking.

Dinner At 4pm:

date night outfit


This is such an adorable girly look. I LOVE this dress - the ruffles are so sweet, and would be perfect for an early dinner in summer. I chose subtle neutral accents because the dress and shoes are so cute and they stand out really well.

Urban Outing:

date night outfit


This is another neutral look that's great for a more casual date - but you still wanna look like a babe. It's got more of an urban vibe to it, so if you're planning to be out in the city, this look is great. The top is so pretty and would look great with the dark jean shorts. The wedges would be super easy to walk in. The Tartlet palette offers neutral shades to compliment the look (it's my go-to palette).

Going To The Game:

date night outfit


Whether your watching his game or a sports team, this is a great look. I cringe when I see girls dress up for a sports game - it just looks ridiculous and out of place (if you're gonna wear heels, wear booties). This look is great for summer - I kept it neutral again, and added in some black pieces for a sexy look. The lipstick is a subtle colour so it doesn't look like you're trying to hard. Aviators look good on everyone, so if you're going to be outdoors you'll look extra cute.

Lunch Date or Afternoon Patio:

date night outfit


Another cute-girly look! This is a fun one for an outdoor date. White is always a winner (unless you're sloppy like me) The necklace has a little bit of blue and pink it, and I chose a poppin' lipstick that will look great against the blue in the necklace. I LOVE the cork clutch because it goes with so many things, but it really compliments this look. This one it all about the waist up!

Evening Events:

date night outfit


This is actually my favourite look. If you have an evening date in the summer, you need to try this. I love the floral print of the heels paired with the leopard clutch. The dark purple lipstick balances with the dark heels, jeans and clutch so the pretty white top stands out. I just want to buy this whole outfit because it's so sexy!