V-Day

Single people generally hate Valentine's Day. Surrounded by couples holding hands, exchanging sappy cards and cheap chocolates it's like having a sign pinned to your back exclaiming "I'm single!". When your cubicle neighbour receives a beautiful bouquet and the only thing you've received is a text from your dad wishing his "cute daughter a Happy Valentine's Day", it's tough not to be bitter.

I choose to look at Valentine's Day as an opportunity, rather than a sad day. It's a great excuse to ask out that guy in your class or someone you've been friendly with at the office. Maybe you've been chatting online with someone for a few weeks but no dates have materialized thus far. What single guy isn't looking for an easy answer to the question "what are you doing for Valentine's?"

A few years back I started a relationship this way. I was working part-time and one of our shifts landed on the big day. Rather than go home alone, I got take-out and watched a movie with a cute co-worker. I proposed the idea to him the week prior, with the context of neither of us having plans, and no one wants to be alone that night. We had a great time and ended up dating for several months after.

I'm not suggesting you ask someone out to an uber-romantic dinner, or expect the guy you're casually seeing to present you with a dozen roses and a blue box. I am merely reminding you to keep your options open and always see the silver lining!

Motor Mouth

I met a guy, we went out last week and we had a great time. I've told my friends about him and of course shared a few details with them. This makes me wonder if he's talking about me. Do boys ask "so any new girls on the scene?" as they are sitting around drinking beer and watching the hockey game? I realize it's probably not how they greet him when he shows up, but does it come up at all? Does he like me enough to say "I met a cool chick and I'm going to see her again next week"? I think I'm a cool enough girl that he should be excited to tell them about me. I guess it depends on a few things: his comfort level with the guys, how many other girls he's seeing and whether I'm on his mind when I'm not around.

The Writing's on the Wall

Some people are great writers. Even more people are great texters and emailers. The problem with this is that you can be tricked into really liking and getting close with someone without actually liking them in person.

Here's how it happens:

• You meet someone and begin an email exchange. This could be a person you met via online dating or at a bar, or even a colleague who you first contacted about a work-related matter.
• You email regularly, with the exchanges getting ever more flirtatious and personal. This is especially tricky when it comes to co-workers - where what began as work-related has now moved to discussing weekend stories and upcoming activities. Maybe the guy has by now casually invited you out for next week.
• You really hit it off with the person - at least via print. They seem funny, witty and there's always a ton to talk about. You begin looking forward to the person's daily emails and rely on them to pick you up during the day. You find yourself smiling when their name pops up in your inbox.
• The problem comes when you meet in person. Maybe you had already met and there was no spark. If it's an online relationship you may not have met yet, in which case there can be disappointment when the written chemistry fizzles out as you sit across from one another. If it's a co-worker, being in a meeting together can be a vastly different experience than what happens in your fantasy written world.
• You need to draw the line somewhere. If the guy is still emailing daily and asking you out, you can't continue to respond "as a friend", knowing that you've already written the relationship off. Just be prepared that you will find a hole in your day when it's 11am on Monday and you haven't heard from them.

Toothbrush SOS

It is too presumptuous to bring my toothbrush with me the first time I visit a guy's house? Yes yes I know it seems like a no-brainer question, but there is more to this question.

First of all, we've been out more than a couple of times, so he's far from random. Secondly, although he's never stayed over, he has been at my place until the wee hours, and I have considered inviting him to stay. Then there's the fact that regardless of who I'm visiting or where I am, it's crazy cold out, and who really feels like walking to the subway at 1am in mid-February?

I think I'll take it...but not tell him. If I get an invite to stay I'll conveniently have it with me, but if not I don't appear to be a crazy. Just when do things get to the point where it's accepted and understood you're going to stay over?

Wife Potential

What are guys really thinking about when they begin dating a girl? Are they looking at the state of her fridge, her dirty bedroom or her inability to cook as signs of her wife potential? Or are they blindly going along, only focusing on how good her butt looks in those jeans or how cute her smile is?

I have a friend who has banned me from mentioning my hatred of all things cooking-related because she thinks it's hurting my chances to get married. I'm not trying to snag a ring any time soon so I don't really care, but it has got me wondering: What are guys considering when they're spending time with you?

If I tell a new BF about spending $200 on a big night out, will they think I'm not fiscally responsible and therefore a poor choice for a partner? When I invite him over but do not offer dinner is he thinking I'll make a bad wife? Fine if these thoughts are bouncing around, as long as he's also considering all the amazing things I do manage to accomplish each day! I, personally, think those things make me a pretty spectacular choice.

Busy Schedule

I am involved in a lot of activities outside of work. In a regular week, I have one volunteer meeting, a business meeting for a start-up I'm working on, a yoga class or two, as well working late and meeting friends for drinks. This doesn't account for the book I'm working on and any extra volunteer commitments I have to spend time on or prepare for.

I choose to have a busy life and have almost always been that way. I think I perform best when my schedule is packed, and I'm really proud of how many activities I'm involved with and how full and varied my schedule in a given week can be.

I've realized that my preference is to date someone who is also involved in several activities. I know this also comes with a downside - it's very hard to find time to get together - but if you like each other enough you should be able to find some time to meet up. I would actually like a guy to tell me he's busy three days of the coming week because he has a hockey game, a board meeting and a guys' night out. That's music to my ears, since by Sunday my week is always almost fully booked. That said, this really is only good if he follows up by saying "I am free on Thursday, and would love to see you then."

I don't think this is too much to ask for - if I can find five things to be involved with, a guy should be able to find at least two.

Video Replay

When I was in gymnastics our coach would videotape us attempting new skills in order to show us what we were doing wrong. It's much easier to correct a tumbling line or bar dismount when you can see exactly where your mistake was, even if your coach has been telling you for the past 20 attempts.

I would like to use this technique on my dates, and would especially like to watch a video of myself on a first date. While I know it would be cringe-worthy, I could probably learn a lot about how to improve my game. Even without video replay I knew I was making some mistakes on a recent date.

Things to remember on a first date:

• Do not refer to your ex-boyfriend as your boyfriend. For example: "I went to Boston with my boyfriend.". While in your head you know that means "my boyfriend at the time", your date is not in your head.
• Do not obsess about being short and only dating short guys. While this is pretty accurate in my case, I probably could have stopped discussing the short waiter and the fact that he may like me because I'm short. Especially when my date isn't that tall himself. Yes, I might have a short complex, but he doesn't need to know that one hour into our date.
• Do not share the story of a creepy friend who repeatedly hits on you. While I'm sure there was a point at the start of the story, I realized mid-way through that I just sounded like I was bragging. Although I don't believe that a creepy hit-on is something to brag about, others might.
• Do not be overly self-deprecating. While everyone likes someone who can poke fun at themselves, I was even annoying myself when I got to the third or fourth negative story or comment about myself. When I entered the bar I felt cute, fun, sexy and smart, but somehow throughout the night I forgot to mention any of the things that make me feel that way.

At this point I just feel relieved that he decided to still talk to me the following day!