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Monday, March 19, 2012

“Helen of Troy” – Testing the Waters of Casual Dating

Miss-Adventures: A Hapless Helpless Hopeless Dater 

What happens when two clueless daters decide to try and navigate their way through “casual dating”?  What happens when you set out with the intention to keep things easy going and in the moment when it goes against both persons’ natural instincts?  On one hand, it sounds perfectly logical, rational and normal to want to take things slow, see where dating takes you both, keep your relationship as breezy and uncomplicated as long as you can, and enjoy the early stages that are filled with wonder, butterflies, sexy energy and romance.  But on the other hand, when you have two monogamously-minded girls who thrive on one-on-one connection but they have both just come out of long term relationships that made them too gun shy to even commit to a dinner date much less an exclusive relationship, it becomes a tricky proposition.  There’s an awful lot of gray area to work with!

In my twenties, I was a fairly active dater.  I enjoyed singledom for many years before I met my wife.  I can’t say that I was ever a good dater, but I did enjoy being single, meeting people and coming and going without accountability.  It suited me well ... back then.  Naturally, I assumed that when my wife and I split, I would be able to slip right back into my old role of single and actively dating gal.  Hmph!  I obviously hadn’t realized how much my personality had changed during the course of my marriage.

At the end of my first date with Helen of Troy, she made it clear that she was feeling gun shy about coupling up again after having just gotten out of a long term relationship.  Totally understandable!  I was in a slightly better state of mind when she and I met but I had certainly been in a similar mind-set not long before her.  So when Helen asked me if it would be alright to take things slowly while also continuing to date other people, I was more than willing to say yes.  It made perfect sense to me. 

I was super excited about Helen.  She had a lot of really great qualities that you would want in a lady friend: she had brains, beauty, humor, a sense of fun and passion for all things in her life.  She was a charming and merciless flirt, and someone you would be proud to introduce to your friends.  She had all that, and we had really good chemistry.

A week after our first date, we finally had plans to see each other for a second date, which was to be a peaceful walk on the beach on a sunny day and then a whole day of just playing it by ear.  In retrospect, a week doesn’t seem all that long but when you’re excited about someone, and all you had for a whole week was flirty texting, suggestive emails, and memories from your first night together, that week can seem to drag by in dog years.  So by the time Helen made it to my place for our date, we wasted little time in deciding to push the beach walk until later on in the afternoon and we headed straight back to my bedroom and shut the door.  Clearly, we had important business to attend to.

Not long at all after we started dating, I asked Helen what her plans were for Valentine’s Day.  Knowing she was feeling skittish about anything too "relationshipy", I didn’t want to put any pressure on her and I was open to doing anything she felt comfortable with.  I proposed that we could be as romantic as she’d like and I’d be happy to take her out and “romance the shit out of her” or if that felt too much, we could do something silly and un-romantic, like bowling or bouncing at an indoor trampoline park.  My bottom line was that she was single and I was single and wouldn’t it be a shame to let that day pass without doing something fun together?  Her answer: “Can I think about it and get back to you?

For the next week or so, we managed to see each other a few more times but I wouldn’t necessarily call it dating.  In fact, we rarely went out when we spent time together.  In retrospect, I’ve come to the conclusion that our relationship wasn’t really “casual dating”, it was more like casual sex and ordering in.  I started to realize that fact when Helen finally got back to me about making Valentine’s Day plans. 

Helen had decided that she didn’t want to get together on Valentine’s Day and that she would rather spend the evening with her friends attending a V-Day burlesque show.  I was totally ok with her wanting to forego the holiday altogether and I understand the implications of spending Valentine’s Day with someone you’re trying to see casually, but then she asked me if it would be alright if she stopped by after the burlesque show so that she could “kiss me madly”.  Now, on one side of the token, who doesn’t want to be kissed madly?  Doesn’t that just sound like a wonderful proposition?  But on the other, the fact that she wanted to spend the evening watching burlesque dancers and then sneak over to my place late on a Tuesday night somewhat smacked of “booty call” to me.

My reply: 

Your evening sounds like a lot of fun and I hope that you have a really wonderful time with your friends.  Gay husband and I have decided to spend a very romantic evening together: we're going to go bowling and get drunk on cheap beer that probably tastes mildly of rental shoes.  That's just the sort of romantics that we are.  ;-)

As for your very sexy suggestion of coming over after your burlesque show to "kiss me madly", as appealing as that sounds, I think I would rather like to save that for an evening when we can spend a little more time together and not feel so rushed.”

Not long after sending this e-mail, we were at my place talking and I brought up the fact that I felt like we could be slipping into “booty call” territory.  I’m not sure it was ever her intention (she swore it wasn't) but the thing is, when you’re casually seeing someone, there’s this very slippery slope you have to be conscious of.  While I was really enjoying our time together and experiencing this fantastic chemistry, I wanted to be sure that we were actually dating and that whatever we were doing at that moment had evolutionary potential.  I knew I did not want to be a late night “booty call” because I liked her.  And I knew that I wasn't interested in becoming friends with benefits because we all know that FWB only works when neither party has any interest in the other outside of the bedroom and, true to form, I could already feel myself getting attached.

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