08/29/2012 09:32 am ET Updated Oct 29, 2012

Dating Tip: Don't Compromise Your Own Happiness!

Taking the next steps in any sort of relationship is downright frightful, and I'll be the first to admit, I was scared. Here's how the next portion of my budding "relationship" played out.

Date #1: Drinks at Dos Caminos
Dating tip: Never get so tipsy on the first date that you spill every personal detail about yourself that should have been saved for a later date.

So Cute Guy From Elevator and I have been Facebook chatting nightly when he finally asks for my number. Three-day rule obliged, he texts me and we decide to take it out of the office and onto the streets of NYC for some sangria. Now I do something that I normally wouldn't do, which is sit back and listen instead of talking his ear off. He starts by telling me about himself, giving me the 411 and all the basics, as I gaze at his perfect white teeth, green eyes and sexy smile. When I finally come to, I realize Cute Guy is getting a little loose with his words and starts divulging details about his past relationships, unsuccessful date encounters and childhood hardships. I find all of this intriguing, but then again, that's me. I am drawn to deepness (or as some people call it, craziness). Was this a red flag? Probably. But later that night, he texted me and said he had a great time. I enjoyed his company and felt he was being honest, so on we go to date number two.

Date #2: Casual Hangout on St. Patrick's Day
At this point, we've been texting pretty consistently every day since the first "date," so I invite him out later to meet up with my friends and me. He comes later that evening with a friend who quickly comes and goes. Now, in the interim before his long-awaited arrival, I meet another guy who I called "Cute Guy From Bar." It turns out that he knows a couple of my friends, and he and I actually really hit it off. A little before Elevator boy shows up, Bar boy takes my number and says he'll call me.

Pretty pleased with this turn of events, I collect myself, and no sooner do I do that than I get a call from Elevator guy saying he's outside and coming into the bar. I'm really batting a thousand with this one: I have Cute Guy From Bar and Cute Guy From Elevator on either side of me, and I have no idea how to handle this situation. I don't normally have to juggle guys. I fail at my attempt to give both equal attention, and eventually Cute Guy From Bar leaves and Elevator boy and I head to his apartment, where absolutely nothing happened (other than me meeting his absolutely adorable Havanese puppy).

Date #3: Social Eatz, aka "The Red Flag"
Here we are at Social Eatz, hitting it off per usual. He's a total foodie like me and picks some delish stuff out for me to try. This night ends with him walking me to my friend's apartment and giving me a tap on the back... like a "See ya later, champ!" He continues with the texting all throughout the next couple of hours, and then it happens: THE RED FLAG rears its ugly head. I won't get too into the next series of events, but let's just say the next four to five hours consisted of the most intense text-a-thon I had ever experienced in my life. Besides warning me that he's no good at relationships, he went full throttle into the future, his fears, his feelings, questioning where I saw this going... and this was date number three! I can't even tell you how exactly it ended that night, but I was totally thrown. I mean, sure he was cute and interesting, but boyfriend material? I was just getting to know him! You would think this would have stopped me in my tracks, which it did -- for a little while. But true to form, I give him another shot.

It got to the point where I was almost afraid to tell my friends what our status was, fearful of their wrath (fearful they were right). He and I continued to see each other consistently for the next couple of months, playing the role of girlfriend and boyfriend without actually acknowledging that fact. We even broke things off (for about two weeks) and then got back together.

We'd be here for days if I went on about every last detail up until the bittersweet end, so I'll leave you with this: Cute Guy From Elevator became more to me than just a friend. I really fell for him and I fell hard. I saw in him things he never saw in himself and I wanted more than anything for him to see himself the way I saw him, value himself the way I knew he should be valued. I compromised my own happiness, convinced I could make him see the light. I think the ultimate and biggest mistake I made was allowing someone who knew from the start that he wasn't equipped to be in a relationship to attempt to be in a relationship. Both of us were at fault, both of us were hurt. It was time to move on.

Letting go of anything you once cared about, becoming comfortable with the uncomfortable and facing your fears are some of the hardest things we have to deal with in life. But for me, recognizing the patterns that I now refuse to repeat because of my experience with this relationship, and forging ahead to become a better person... well, now that's what I call becoming fearless.

For more by Samantha Selvaggio, click here.

For more on becoming fearless, click here.