In Which: I May have kissed a 50 year old (or why wine and I are friends)

So Yeah- You read the headline right. I  went to  a wine centric event the other night.  It was great, on many levels.  I got to try some great wines, got to meet some great people, and stumbled into two great conversations with two very different guys.

Guy A was a young dad, who adored his children.  We had a great time chatting, and talked almost half the night until he had to start heading home.

Guy B was an attorney.  He was also in his 50's.  We got to talking about law and the constitution, and before we knew it, we were closing down the event.  I was going to catch a cab home, but we were still talking so, we walked and sat on a bench, where we talked for another 2 hours.  In this time, I learned a lot about him, and we connected a little bit.  To the point, where we kissed.

Yes, I kissed a 50 year old (or as the BFiC would say Silver Fox). 

  Side note:Apparently silver foxes are so popular they have their own site?   

I didn't really think much about it until I got home, and realized with a laugh, that I had indeed made out like I was in high school several times along the walk to my stop, without caring how old he was or whether or not this would equal a relationship.

Which, regardless of what happens, was kind of a wake up call to me-but in an entirely good way.  I went to this event without any pretense on trying to meet someone.  This was strictly about the wine (because let's be honest- wine and I have a far truer relationship than I feel I am likely ever going to find) and I just wanted to have a good night.   And the next morning, I could count two guys who I felt I had completely worked my mojo on, completely unknowingly.  I really need to trust myself (and maybe the wine) and know that I am awesome and have a personality worth knowing.  That's just hard for me to believe.

Why? You may ask...

I do what I do (work wise-marketing) because there is a set of rules, and I know how to play in that sandbox. Business conversations are well known to me.  I'm good at spin, feigning interest in a conversation, and reading between the lines.   Same with when I was in sales.  However, when it comes to relationships, particularly romantic relationships, I feel like everyone else was given the handbook with play by play instructions, and I'm stuck reading one page of the knock off brand of cliff's notes.

I'm awkward and have no concept of whether or not I am flirting, or even if I'm on the receiving end of it.   Meanwhile, the next day, I'm still wondering if I should suck it up and take a step toward letting the guy know I was interested (particularly in Guy A- we had a lot more in common).  But I have no idea how to go about it, without making myself ridiculously vulnerable. 

So anyway, new goal is to be much less prejudice about who I'm willing to talk to, or see as having potential. I've already made a rule, that if someone has enough gumption to ask me out on a date, I will give them the shot.  This rule was made after I was in sales a few months, and realized that I had no right to be upset with people who wouldn't at least give me a shot to tell them about my product, when I wouldn't give someone a shot in real life.  I also need to learn to get over my fear of rejection for something as little as asking a great guy if he'd like to have another great conversation....Yet, here I sit at the crossroads, regularly checking his profile, as if I should be receiving something, and yet too scared to send him something myself. 

What do you think 20 somethings?  What's the largest age gap you've had? 

Meanwhile- he wasn't half bad at kissing...

P.S. Wine and I are friends because wine introduces me to myself on a regular basis.  Wine makes me confront different aspects of myself (both good and bad-oh how I wish I could skip the bad).  Wine is also delicious...