I’m pretty clueless when it comes to dating.  Before my last boyfriend I never went out on dates—ever!  I flirted and fooled around with boys, but I never went farther than a first date with anyone, and that’s including my ex!  I’m sure my low self-esteem issues didn’t help, because believing no man will ever love you really attracts potential sexy-time friends.  I focused my energy on things other than boys, and was rewarded with great friends, excellent career opportunities, and a pretty handy vibrator!  But of course, I also felt on the outside when my friends met someone new, fell in love, and got engaged.  I could never relate to these feelings, but I desperately wanted to.

It’s been over two months since my ex and I broke up.  Two months where I spent too much time reflecting on what happened and if it could have all ended different.  I’m going in the right direction, but I still struggle with the “letting go” part of the break-up (yes, that means online “research” whenever I get bored or a case of the sads).  Thankfully I’ve spent a majority of my post break-up time working on new projects and dipping my toe into the dating world.

Now that I’m single again, I’ve started to enjoy dating, even if I’m completely clueless as to what I’m doing.  I’ve met some really great people, and I know what I want (and NEED) in a partner.  I know I’m attracted to smart, witty, (hopefully bearded men), and the hilarious thing about all that is now I’m slowly learning how to approach these types of men.  I’ve started to go out more and put myself in situations where I’ll meet men that I’m attracted to, rather than just fantasize about meeting them.  It may sound like I’m the blind leading the blind or I’m saying the complete obvious, but it takes experiencing these things for them to click.  I could listen to someone say all this stuff to me until my ears bleed, but it’s a completely different feeling when you’re in it.

I may have “slutted” it up a bit post break-up, as I threw myself out there and wanted to learn what sexually drew me.  I struggled with not going too far in my sexual fascination—it’s really not a good idea for someone who is interested in rougher sex to jump right into that with someone she doesn’t know.  It’s possible to get yourself in over your head before you are able to deal with the ramifications.  You need to ease your new partner into these things, not jump in head first.  Even if that person seems responsive, the two of you could do more harm in the long-run to your relationship.  More times than I’d like to admit I’ve chosen to lose the mystery and use all my tricks on a guy because I was too afraid he would run at his first chance.

I’ve tried building a relationship from a one-night stand, and it is incredibly difficult.  My own sexual desires conflict with my desire to be in a stable relationship.  In the end, it’s all about recognizing what you want and finding someone who can give that to you, and who you equally want to give back to.

Gwen will post some of her more amusing dates in our NerdyPerv’s First Dates section.  So come back, and laugh with her!!