If you read My Dating Journey: Could He Be the One? then you know all about my love-at-first-sight-ish experience with Nathan, a skater boy who stole my heart. You also know how nervous a rebellious, popular girl, Mercedes, started making me feel. Despite the nerves, I continued to text and hang out with her (though the two of us never hung out alone). At first, our conversations were innocent; after a while, they became more and more flirtatious. 

The flirting intensified as time went on, and I didn’t feel guilty about it since Mercedes was a girl. Moreover, I realized that my nerves weren’t the negative, something-bad-is-going-to-happen nerves. They were more like the nerves that you get when you’re around a crush. One night, after dating Nathan for about a month, Mercedes asked me – only me – to come to her house to drink. I couldn’t say no. More Here...

Okay, I have a serious problem. I knew this would happen.

I have recently gotten back together with my ex, though not “officially” yet. It's up to me to ask him out this time because he is giving me the freedom to stay “single” as long as I desire, since he was the one that horrendously fucked it up last time. Anyway, I was thinking about ‘asking him out’ this Friday. The only problem is... I have a skeleton in the closet and I don’t know when the best time to clear it is, if ever. More Here...

When I lost my virginity, I was 16, drunk, and contorted in the backseat of a car. The girl I was with had driven us to a secluded cul-de-sac, and it didn’t take us long to steam up the windows and lose track of time. Even though she didn’t know it was my first time, she was super careful, and kept checking with me to make sure I was okay. Afterwards, we drove to a gas station so I could fix my bra and sex hair, and I spent the night at her place. 

At the time, losing my virginity was a big deal. But looking back, I wonder: “What was the big deal, exactly?” In high school, losing your virginity is the elephant in every dark, poster-laden room. And seriously, there are more movies about swiping (or neglecting to swipe) your v-card than I can count. Our culture makes losing your virginity seem like such an event, but when it comes down to it – is it? Is losing your virginity overrated? More Here...

A little over two years ago, I cheated on my now-fiancée. I was away at a conference for a few days, and had a girl sneak into my hotel room one night. Though we didn’t have sex, we touched each other under the guise of the States game (when Person A thinks of a state, Person B guesses, and with every wrong guess Person A slowly moves their hand up Person B’s leg), and we definitely crossed a line.

I’m not proud of what happened, and to this day, I feel awful about having hurt Mercedes. And get this – when I was away fooling around with another girl, she was buying my engagement ring. I’m the worst person in the world, I know. But here’s the thing: I never had feelings for this other girl. I wasn’t attracted to her. In my case, I think physical cheating is all that happened. Wait, is that even a thing? More Here...