05/04/2012 05:02 pm ET Updated Jul 05, 2012

Dating Without Fear

Four years ago, the guy I was seeing -- JJ, my best friend in the world -- committed suicide. Rather than deal with the loss, I did what I do best, and I immediately jumped into a new relationship. That relationship ended in disaster when I caught him cheating on me with not one but two women. Before I even got the chance to call him out on it, he "broke up" with me... by sending me an email and changing his relationship status on MySpace. I mean, really, aren't we supposed to be adults?

After that, I went on a bit of a dating hiatus. Let's be honest: If that's what's out there for me, who wants to even bother leaving the house? And so, I finally let myself come to terms with JJ's death. By "come to terms" I mean that I adopted an oxycodone habit that I coupled with drinking my weight in alcohol. About five minutes before I was probably going to get fired from my job and OD on my kitchen floor, I picked myself up, threw myself into therapy and got it together. And, wouldn't you know, a few months later, I met Army Boy.

When I found out that he was being deployed to Iraq a week later, this of course seemed like the perfect relationship to me. Makes sense, right? It was actually the anniversary of JJ's death, and Army Boy brought me breakfast and spent the whole day with me. It's still one of the nicest things anyone has ever done for me, and he actually turned out to be an amazing person. A week later, he was in Texas preparing to go to war. He flew me out to Fort Bliss (seriously, that's the name -- how cute is that?) to spend his last week in the States with him, and it was an incredible trip. I climbed a mountain, made a friend I believe I will have for a lifetime, ate at the greatest steakhouse ever (there are actually cows outside) and, oh yeah, got knocked up. I found out about a month after Army Boy left. We were picking out names and planning to move to Florida together when he got back from Iraq. And then I lost the baby. And it went from really, really good to Wes Craven nightmare. I never knew that someone who told you they loved you could cause so much hurt. I swore off men forever at that point.

"Forever" lasted about six months, which is when I met a very cute bouncer at a local bar who made me smile. So what if his ex was pregnant with their baby? (Are you catching on that I don't have the best judgment when it comes to my love life?) This wasn't going to be anything serious for me anyway, just a way to get back into the game. Until I then met a very sexy bartender who happened to work at the same bar as the bouncer. Tricky, but not impossible. I eventually chose the sexy little bartender, who, although he has a wonderful heart and it was well worth the sex (who knew I could still manage to do it in a car at 28 years old?), turned out to be a huge waste of my time. And the bouncer? He now has a very beautiful little baby girl, whom he sends me pictures of every now and then. And he is back with his baby's mama. Obviously.

While I was still open to the whole dating experience, I had given up hope at this point that there was still the "nice guy" out there. And then I met Doc. He was handsome, funny, kind and... a doctor. Too good to be true, right? So, after playing coy for weeks, I finally agreed to go out with him, and it was pretty much an insta-relationship. I could tell him about all of the baggage from my past -- let's face it, I come with plenty -- and he barely even flinched. He was just a great guy, and I really thought it would last forever. Until it didn't.

See, the thing is, it really is all about timing with relationships. My family will waste no time reminding me that I'm in my 30s and not getting any younger. How I even manage to get out of bed in the morning is a mystery, right? Well, I never thought I wanted children until it almost happened, and then it became all I could think about. I swear, I think I'm a step away from lactating when I hear someone else's baby cry. It's sickening. But Doc is four years younger than me and not ready to take those steps yet. I can't blame him, really. When I was his age, I was living in Fort Lauderdale, dancing on bars and hooking up with the drummer in the band. If someone had tried to get me to live with them and pop out babies, I would've joined WITSEC. And so, another one bit the dust.

At a time when I thought I would have already published a book, married the man of my dreams and traveled the world, my life couldn't be further from that -- but things could be worse. I actually gave in to the world of online dating. After all, how much worse could it get? While it's still early, I am now in a relationship with someone who has made me happier than I remember being in a very long time. Whether or not there is such a thing as fate or soul mates, I'm not sure I'll ever know. But at the end of the day, I haven't given up hope. Maybe that makes me fearless, maybe it makes me a fool. But it's what gets me out of bed each morning. That and cinnamon dolce lattes.

For more by Kaylee Scottaline, click here.

For more on becoming fearless, click here.