Waiting, Doubting

I have learned the lessons of He's Just Not That Into You, and I understand that if a guy really likes you, he'll make the effort to find you and ask you out. Even though I'm well-versed in this area, I've always found it tough to sit around waiting for a guy to make a move, and especially to trust that a guy will make a move. I guess I don't give them, or myself, enough credit, but I often feel like nothing will come of a first encounter unless I take charge of the situation.
Many women believe that taking things into their own hands is the right way to approach dating. Unfortunately, being the first to call or message a guy means you are putting yourself out there, and then leaving the ball in their court. Once that first message is left hanging in the air between you, there's not much else you can do without seeming a desperate stalker. Although I convince myself it's best to be proactive in dating, I end up being much more doubtful of myself after getting no return message. I would have been better off risking my chances and waiting for them to reach out. At least then I could have convinced myself that I was impossible to track down.

Is This Your Stop?

Nearly every day this winter I've seen at least one attractive young guy while riding the subway in the morning. I have wanted to approach them - not always for me but maybe for one of my friends - but I'm not sure how. I've made eye contact over a few stops but let's be honest - someone has to be pretty brave to approach a stranger on a crowded subway. Not to mention that every stop brings the possibility that your crush is going to get off: it's not like we all wear signs announcing that we're exiting at St. Andrew's so they only have two stops left to make a move!
I've come up with a few possible ways to break the ice or initiate a conversation but I'm not sure I'll be trying any of them out soon.

• Accidentally fall into them when there's an abrupt stop
• Sit beside them and ask them to hold something for a moment as you kerfuffle with your giant purse
• If you exit the train at the same time, strike up a conversation as you're exiting the station
• Make fun of someone else on the train. I know that's not very friendly, but there are always an array of amusing people and rolling your eyes with someone can be a bonding experience!

My last resort is making up cards that say "you're hot, come to my mixer next month" so I better come up with some better conversation starters, stat!

Chat Room

Speaking with someone for hours on end, whether in person or online, allows you to really get to know them. Someone who is witty, funny and seems interested is so attractive, they'd catch my attention even without knowing what they look like. It's amazing that some people can make me want to chat forever - just by asking questions, replying promptly, and making me feel pretty (without seeming sleazy) I end up going to bed an hour later than planned.

I guess this is the benefit of online dating - it gives people a chance to get to know each other without all the focus being on the so-called chemistry or physical attraction. What I've discovered is the benefit of meeting someone through an alternate online channel: they're not necessarily out there with the sole purpose of meeting a girlfriend, hook-up or date. Having a chance to innocently chat online, be it via Facebook or email, allows people to have a regular conversation or make a new friend.

It's not every day I meet someone who can keep up with my comments and who can make me literally LOL. Technology and various chat platforms make it especially difficult to show your sarcastic side without appearing as a plain old rude girl, so when a guy 'gets' me it really counts for a lot.

Even if he's not my usual kind of guy, maybe it's worth seeing if the chemistry translates to real life.

Relationship Hangover

After my latest break-up I felt relief, excitement and the feeling that comes with knowing you did the right thing, even if it wasn't the easiest thing. Now, months later, the sadness is creeping back in. I knew this would happen, but it still stings.
While everyone was nicely concerned about me in the weeks that followed, I felt, for the most part, perfectly fine. But a few weeks passed and reality sunk in. The seemingly endless list of available guys I know or could meet has shrunken, my body is tired from wearing 4 inch heels on every outing, and my cheeks hurt from flashing my best smile at every guy I pass on the street.
The more important thing is that it was the right decision, and I know that we all have to go through some tough times every now and then. But the initial high of being free and having my own life back was the equivalent of 1am at my favourite bar, 5 drinks in, and now I'm experiencing 9:30am the next day. The relationship hangover. Sometimes a reliable, quiet, alcohol-free night is the way to go after all.

Looking Good

I have wavered on this as of late but I keep reminding myself how important it is to ensure I look good when I leave the house. I'm not talking about spending hours doing my make-up for a quick trip to Rabba, but you never know who you'll run into when you're out and about. I always seem to run into an ex or stand next to a hot guy on the subway when I have no make-up on and I'm wearing my worst pair of jeans. Impromptu after work drinks or last-minute dates always happen on the days I chose to forgo a shower and my hair's a greasy disaster.

I love sweat pants and I happily go out shopping in them. But from now on I'm going to ensure they're cute, flattering sweats, and not my men's size x-small from Wal-mart. Maybe it's a bit of extra mascara or some lip gloss, but when I do run into Mr. Right I want to make sure I can grab his attention - in a positive way!

Seeing an Old Friend

I'm sitting at the bar with a glass of wine, waiting for an old friend to walk through the door. It's been about two years since we've seen each other, and all I can think about is the great chemistry that always existed between us. Nothing ever happened between us...but who knows what tonight will bring.

I wonder what he'll think of me. Do I look fatter than before? Is my hair too blonde or not blonde enough? Am I wearing the right outfit? I went for casual with (what I hope was) some sex appeal...should I have dressed up more? Then there's the bar. So many options in Toronto - Is this a good spot? It's dark-ish and busy, and candlelight always lights up my eyes, so I think it was a good call. But maybe it's too loud, or I look too slouchy since I'm sitting on an awkward bar stool. But then there's the benefits of sitting on bar stools - our knees will inevitably touch and we can lean in to hear each other without a table getting in the way.

I hope he still thinks I'm pretty. I wonder what I'll think of him. Will I still think he's cute, charming, funny? What if we run out of things to talk about 15 minutes after his arrival? What if what if what if...and then he sits down beside me, he jokes about being late and all those crazy thoughts just disappear.