I hate dating. With a passion. All of the "special" people from my past, conveniently skipped the "dating" part and went straight to the relationship part. Maybe that's why each relationship exploded so quickly. Nevertheless, I continue to avoid dating if at all possible. I find it exhausting and I'm not particularly good at it. I never know how to dress "up" and still be myself since I'm relentlessly casual on a daily basis. I'm fairly good at small talk, but find it so draining that after one date, I need a full week to recover. I'm awkward with sharing information about myself, due to years of being bluntly honest and ridiculously standoffish. 

My cutie roomie, however, is a dating pro. She's able to meet several men for coffee, drinks, or dinner and assess whether they are boyfriend material with a gusto I can't muster. She tirelessly comes home from work, fixes her hair and makeup in minutes like a modern day supergirl, and meets candidates with bubbly energy and a beautiful smile. Her optimism for each of these lucky fellows is contagious and I find myself cheering for each potential boyfriend week after week. That guy is Super Funny Man. This one is Sensitive Music Lover. She tends to like Mr. Intellectual & Witty. 

My dating life looks more like a gas station on Route 40. You're deliriously happy to see it if only to break the monotony, but at the end of the day, it's just a gas station. You fulfill your purpose and move on quickly. 

Most people who know me well agree that I don't give off the best first impression, but once you get to know me there is loads of fun to be had. Unfortunately, dating is all about first impressions and portraying yourself in the best possible light. It's not that I can't be nice or funny or energetic; it's that I lack the optimism to think a stranger is worth it. 

However, these days I've been thinking about adjusting my style to mimic my roomie. Statistically, I have a better chance of a successful relationship if I meet and date more men, right?  But where does the energy come from? 

~~~~~

I know what my roommate is talking about. The bulk of my relationship happened the way they do in school - you fall into it. It is all proximity, there is no real "dating" involved. But when I found myself single at 27 for the first time in 7 years, I thought I should probably figure out how to do this "dating thing". Shows like Sex and The City made me equally excited and terrified to be a single twenty-something in a major city. But, join or die (alone), I guess. 

And my lovely roomie is right - dating, even for us eternal optimists, can be exhausting. So very, very exhausting. There are always going to be those dates that are as awkward as a bad job interview. There will also be the dates where you meet at 7 for dinner and end up closing a bar down because you have so much to say to one another you don't notice the minutes whizzing by. Even when the amazing dates don't end up going the distance, the very fact they can happen is reassuring. 

For me, dealing with both is as simple as mind over matter. 

If all we wanted was to be married, we would be. We are modern women who know how to get what we want, and most of the time, we do. Most of us want to be happily married to someone who is our partner, our best friend, think we are the most gorgeous creature to walk the earth, challenges us, loves us, and wants to grow old with us. No small order. Heck, we all know people who are married for the sake of being married. And I think we can all agree that holding out is always preferable to settling. 

There are times where I want to go home, eat pizza, hide under the covers, and give up. It isn't pessimistic behavior, it is normal and human. But there are times where I want to get dressed up , have a glass of wine while I do my makeup, and embrace the butterflies in my stomach. 

Every first date is a chance at a new beginning with someone, and with any luck, it could turn into a happy ending. But either way, go out there, look smokin', let someone buy you dinner, and give him the privilege of being able to brag about going out with a goddess like you. Hell, you probably made his day.

~~~~~

Ali's dating tips:

I have found that the best formula is to be "yourself-plus" - you, just the best possible version of you. Clearly, you must be yourself, because you want to make sure your personalities genuinely click. But leave the first few dates for fun and flirting. Don't yammer on about your insecurities, or make awkward jokes about being unmarried or barren. I am happy and bubbly on dates, because that is usually who I am. Anyone who has seriously dated me knows that I have dark thoughts, real fears, and serious moments. Things like family divorces, eating disorders, bouts with depression, or whatever particular baggage you carry can come later, when you are bonded and in a real relationship. 

The beginning is supposed to be the fun part. Fireworks, nerves, and chemistry may be scary at times, but to be honest, it is also what you fondly miss years into a happy coupling (and somewhat wistfully envy your single friends still experiencing it). Be yourself, just the most fun version of yourself. If you are wry and sarcastic, great, make some funny cracks. But don't get all Debbie Downer on them just yet. If you are a party girl, super, knock a couple back, but don't start doing shots and trash-talking him like a frat boy. 

Most importantly, go into every date with a positive attitude and the energy will magically appear!