From the moment I heard about Kevin’s divorce, my interest was piqued. I had known him for about 10 years, and although our interaction had been limited (we used to work at the Saturn dealership together), I had always been impressed with his humor and values. So I called him to extend my condolences about the news. It sounded like a harmless gesture of support, but my intentions were not honorable. Then I dropped a seemingly innocent sales pitch to lure him to the dark side: “You are new to the single world, and I have always been single, so who better than me to show you the ropes? I know the cool things to do, and can be a good friend.” Despite the logical approach and caring facade, it was pretty obvious that I wanted more than friendship. He wisely rejected my offer to mentor him on how to have fun, wondering to himself why a co-worker from his past would be so bold.

Over the next few months, I continued my attempts to woo Kevin, with no success. He has so much integrity that he wanted to wait until the entire legal process was complete before starting anything with anyone. While this was very admirable of him, it was very inconvenient for me. We now call these months “the time when Kevin was blowing me off.” Finally he acquiesced, and we arranged to go together to check out the First Friday festivities downtown.

I didn’t hold back: I bought a new outfit and set out to look hot. I had high hopes for this date. I was still stinging from the burn of my past relationship (a word I’m using loosely here) and was anxious to start hanging out with someone new. I’ll go ahead and admit I even shaved my legs for the occasion.

Kevin brought flowers, which was incredibly sweet. I have received alot of flowers in my time, mostly for my birthday and Valentine’s Day. But when I try to picture someone bringing me flowers for a date, my mind draws a blank. It seems like an old-fashioned but incredibly romantic gesture, one that has fallen out of fashion. I was touched.

Unfortunately, the evening took a nosedive from there. You can imagine how much Kevin’s head was spinning; he was in courtship mode for the first time in over 20 years. His heart was still hurting from the failed marriage, and he was having a hard time thinking of me in a romantic way. Ever since he had known me, I had been in the category guys normally reserve for females who are relatives, or best friend’s spouses. To steal a phrase from the second Clerks movie: I was “persona non-nookie”. This combination spelled disaster, but I didn’t know it yet. At this point I was just putting the flowers in a vase and hoping for the best.

We went downtown, walked around and tried to get caught up on each other’s lives since I had left Saturn to work at Lexus. We ran into a few people who seemed confused to see us together, including a former Saturn co-worker who was unaware of Kevin’s divorce. Mostly we just walked and talked, until we finally landed at the Pizza Joint, where we talked some more.

Perhaps I should say Kevin talked. He went into great detail about Forrest and Melissa and the marraige and the break-up. He told me how she had asked him to move out of their house on Valentine’s Day, and other heart-wrenching details that are too personal to share here. Sitting across from him in the Pizza Joint booth, I saw an amazing man with a broken spirit and confused heart. I realized that my intentions for this evening were totally different than his intentions, and I felt superficial and guilty. I had not considered the possibility that he would need me to be the friend I had promised to be in my sales pitch. I hadn’t considered it because I was in my selfish, single-person’s bubble, just looking for the next fun thing. But this was real to him, and it was a big deal. Kevin wasn’t ready for dating yet, and he certainly didn’t need to date a 41-year-old with a track record of causing nice guys like him to turn into emotional puddles of mush. I didn’t know how to fix people’s damage; I only knew how to cause it. He was scaring the shit out of me.

He knew it, too. At some point, I think I completely stopped talking and just let him ramble. In addition to feeling afraid, I also felt sad. Sad for him going through this pain, sad for me having caused it in others, sad for both of us to be on a date during such different times in our lives. I felt horrible that he needed to talk, and realized that he had probably not had an opportunity to open up about his heartaches for many years. I kicked myself for not being more sensitive when I was hounding him for a date for the past 4 months. Of course he didn’t want go out with me sooner! He was still in love with his ex-wife and harboring hope for a reconciliation. All he needed from me was an ear and some friendship, and I was ashamed at myself for chasing after more.

In the end, I spent four hours listening to his sadness, and it was clear to me that our first date was going to be our last. There was no way I could have romantic interest in someone that fragile. We hugged at my apartment door, and I watched through my second-story apartment window as he walked back to his car. What a shame, I thought. There is so much I could have taught him about relationships. Little did I know, that in a very short time, Kevin would teach me about relationships. Instead of me teaching him how to be single, I would be his student, learning how to open up to someone in a real, honest way.

The first lesson he had to teach me was about communication-not being afraid to say the tough things. The day following our tragic first date, he called to invite me to lunch. Over Barbaritos burritos, he asked if our date had scared me, and I admitted that it had. So we talked about my fears, and his fears. In that one conversation, he showed me more raw honesty than I had ever seen before. He said he was not looking for the next Mrs. Maskey. He just wanted to take it slow and see where this would lead us. He thought we should give it a try. I was impressed by his courage and his forthright approach.  Kevin was not fragile, after all. Kevin was smart, and honest, and strong.

As a result of this conversation, I decided to at least open myself to the possibility of some kind of relationship with Kevin. He made me realize that I had jumped to conclusions too quickly.  I was blown away by his ability to initiate a healthy conversation, something very few people-myself included-can do with ease. In the course of one shared lunch, he showed me the potential for the Kev-Ang story, and opened the doors I had shut so firmly at the end of our date.

So when he asked me out again, I agreed, and the lessons continued from there. The education of Angela would turn out to be an amazingly fun adventure. Stay tuned!