Step 2. Casual texts are exchanged about: The A.D.D. Weather (Really? -20 to + 12, back down to -5? Thanks global warming!). Calderon leaving the Raptors (Sad face).  And whether or not Beyoncé really lip synced at the inauguration (Spoiler alert- she did).

Step 3. He finally gathers up the courage to ask “Did you want to go out sometime?”

You smile from ear to ear as you reply back with a cool and casual “ Sure, what do you have in mind?” But, the truth is, your brain just exploded:

“ Finalllly!! About time he asked me out.. gosh what am I gonna wear? Who cares – I want to date a guy that doesn’t judge me by my appearance. I am a woman, hear me roar! Ok really, the concept of dating is so weird…what if he’s weird? What if he thinks I’m weird? What if he’s a totally Amma’s boy?! Ok really…calm down. First things first, what am I going to wear?? I need something that shouts trendy, but subtle…independent yet romantic. ..SEXY but definitely not scandalous. Argggh there’s absolutely NOTHING in my closet for this… I need to go shopping. NOW!”

As superficial as it sounds, and as much as we don’t like to admit it, we know that first impressions count. We know that the right outfit can help boost our confidence just a tiny bit, especially in situations when we’re a little outside our comfort zone.  We know that a sense of style is a reflection of who we are. Frankly speaking, it’s just nice to know that a person put in a little bit of time and effort to look their best.

I’m a huge fan of casual first dates. It’s a great, informal way to get to know each other, while doing some sort of fun activity. It’s definitely not as intimidating as trying to get through a 4-course meal, sitting across a complete stranger.  So here are some of my outfit inspirations:

The best first dates are meant to be a little awkward. So be open minded, ask questions, handle the bill gracefully and most of all try your best to HAVE FUN.

Hey, even if it doesn’t work out, at least you looked damn good!

Stay tuned next week as Allan and I team up to list some of our favourite casual (and cheap) date ideas.