First Date Fashion

Whether it’s a first date or the tenth one, picking an outfit is sometimes the most difficult part and I never seem to have the right mix of casual but sexy cool outfits!

If you’re anything like me, you have a closet half full of “cute tops” you grabbed last minute for a hot date that you’ve worn maybe once or twice.

**I think you should wear what makes you feel sexy but comfortable. There’s no point in trying to look like anyone other than yourself. If your date doesn’t like it, they can shove it. (Or, you know, you’re not a good fit.) It will only cause problems down the road if you put on a show.

I’m no fashionista and in all honesty, I think you should wear whatever the eff you want and be yourself but if you’re looking for a few suggestions, I’ve put together a few ideas.

Sporting Events:

Sporting events are awesome and plentiful in Toronto. Our fans are committed and rowdy. Whether you’re going to see the Jays or the Argos, or headed to a TFC game, it’s going to be light hearted and fun. It’s a great first date in my opinion. There’s the opportunity to talk and flirt, but also the safety net of the game if your date isn’t so chatty. (or not your type)

I try to stick with something cute and sporty. I have a pair of white Puma ballet flats that usually do the trick for standing for long periods of time. I think converse or keds would be a cute alternative. I’m a jeans and t-shirt kind of girl when I’m off the clock so this is my element.

Oh, and dress in layers if you’re going to be outside at night (cool breeze off the water for TFC games or the dome could be open for the Jays) AND, top it off with a team baseball cap for a winning look. (see what I did there?!)

Active Date:

I have yet to figure this look out. I have a potential active date coming up, a bike ride, so I searched bike fashion on Pinterest. Why all the skirts?! I’m not a seasoned biker so I’m thinking I will stick with something like this…


I feel like coffee dates for first dates are becoming the norm, especially for online dating. It’s kind of like the pre-date date to determine if you want to go on a real first date. Sometimes it’s the prelude to dinner or another activity but it’s also a buffer so you can get out if it’s not a good match.

I try to keep my coffee date looks casual and rarely do activities after (save the real first date for another night) Again, I’m all for jeans and a cute top or blouse. I have a favourite pair of Levi’s boyfriend jeans from a bazillion years ago that are my go to.

After Work Drinks:

This one is tricky because you have to look good ALL DAMN DAY. (not my forte) And this look only works if your day job includes working at a stuffy office like moi.

Hint: bring deodorant, your toothbrush and toothpaste, and your make-up to touch up post work before heading out for this date.

I usually opt for a pencil skirt and blouse with heels. A slouchy belted shirtdress, à la numero 3 (pictured below), is another great option and allows some eating room. Pencil skirts don’t hide much of the lower belly pooch if you know what I mean.


My go to outfit for dinner dates as of late has been this Joe Fresh dress in white and navy (pictured in the centre below) with a jean jacket and depending on the boy in question, wedges or sandals.

Okcupid and POF let you know a guys height, and me being 5’4″, more often than not I can wear heels. With Tinder, unless they’ve listed it in their blurb, I play it safe in flats. If you don’t give a sh*t, wear whatever you want!!

The following are other great options. If I know I’m going to be eating, I tend to opt for a shift dress to hide my food baby like the first two options below. (Eating seems to be a real concern for me) The best part about dresses, is you can throw on heels if you’re going somewhere a little fancier, or flats for some casual sushi. Mmmm….sushi.

Do you have another type of date you need help with an outfit for?? Let me know in the comments and we’ll help you out!

– A


What to Wear When it’s Hella Hot Out

While it hasn’t exactly been a scorcher of a summer here in Toronto, yesterday was one of those heat alert days! What’s a girl to do when it’s a hot summer day and she has a hot date?!

If you’re ballsy enough to go to the beach for a date, (you sexy minx, you!) wear a cute suit and cool off in the water. Don’t forget the sunscreen!

If you’re super confident, how about a loose crop top and cut-offs for a casual date? Those damn thighs are gonna rub no matter what you wear, am I right? Want to cover up a bit more? Loose fitting top tucked in a bit with cut-offs works just as well!

Ladies, MAXI DRESSES! They are like pajamas but you still look fancy. Just go with a pattern or a darker colour to hide the under boob sweat, k?

Or if you’re short like me and feel frumpy in a maxi, try something short. The less form fitting the better.

You’re welcome!

– A

The First Message

Other than your profile and your photos, your first message is your first impression.

Gentlemen, a public service announcement if you will:

from what I’ve experienced first hand AND heard from friends, women get bombarded with messages on dating sites. It pays to take some time to craft something witty and thoughtful.

This also means the ladies are less likely to message you first. So if they do contact you first, keep these points in mind for your response as well.

1. Don’t be lazy. Don’t copy and paste. First of all it’s pretty obvious. Secondly, you get about as much effort back as you put in.

2. Read their profile, put in the time, compliment a feature or specific photo. Be funny, witty, or charming. (or all of the above if you’re perfect)

3. Don’t propose in the first message. This is both literal and figurative.


A Literal Proposal


A Figurative Proposal  #nopressure!!

A Figurative Proposal


4. Spelling and grammar count.

5. Make me laugh if that’s something you’re good at.

6. Ask a question. Give me something to go with other than ‘how are you?’ Something that requires a little more thought and maybe says a little more about a person. This shows that you would like to get to know me better. Riiiight?

For instance, a potential suitor once asked me the top 3 places I’d like to visit. This may seem a little generic but I think it’s kind of telling of the person you are. If they say something like a Caribbean resort and you’re more of an adventure traveller who would rather go ziplining in Costa Rica than sit at a pool, then maybe you’re not compatible.

7. If you just say ‘hey’ or ‘how are you?’ you’re not likely to get a response 99.9% of the time. The other 0.01% of the time is if you are super good looking and we are crossing our fingers that maybe you are a good conversationalist but were just out of witty things to say at that moment.

8. No matter how funny or cute your message is, if I check out your profile and am not attracted, I’m not likely going to reply. Thems the brakes.

Now go message that gorgeous gal you’ve been eyeing!

**Most of these suggestions are my personal preference as well as feedback from friends so take it all with a grain of salt (and maybe a shot of tequila ’cause it’s Friday!)

– A


After sifting through many a Tinder, OkCupid, and Plenty of Fish profile, I’ve come to learn a few things about photos. If I could give the men of the online dating world some tips on their pictures, these would be it. The following are my own opinion as well as a consensus from my female friends.

1. My best advice is to actually read that page on each site that tells you how to build your profile. You know the one, on POF there are actually videos to help you. They made those for a reason! Watch them, read the information, follow their advice.

2. For the love of God, SMILE in your photos. All of them. Y’all look like serial killers otherwise.

3. Enough already with the ab photos. I get it. It takes serious work and dedication and yes it’s hot. BUT, if you think that’s going to attract the dating/marrying type (assuming that’s what you’re looking for)…maybe it will, but probably not. I’m trying not to judge harshly or be mean, but I need to be honest if I’m going to help you. It makes you look douchey, shallow, and self involved.

4. Do include a full body shot preferably doing something active or sporty but also make sure we can see your handsome face in most photos.

5. Group photos: one or two is fine. It shows you have friends which is a huge plus (seriously). But if I have to play a guessing game I’m going to swipe left. Same goes for pictures of you in the club with lots of attractive women. It makes you look like a player and doesn’t make me think “wow, you can get such hot women I want to date you now.”

6. A word on selfies. They exist. I have one. But it’s not at the gym or in my bathroom. And it’s with my dog….seriously borrow a cute dog (but enough with the sedated tigers) and you’re golden. If you don’t hang out with people enough to have a decent photo of yourself that isn’t a selfie…I’m going to think you’re a serial killer.

7. If you say you’re outdoorsy and like camping or running or whatever….try including a picture of you doing that. First of all, proof. Second of all it’s confusing if all your pictures are of you in the club when you say what you really love is wind surfing.

Along with my personal experiences, I will continue to offer my humble advice and opinions on messaging, profiles, and general etiquette. If you have any questions, please don’t hesitate to send them over. If you are wondering, someone else is too!