not sure what I’m looking for; only know that I haven’t found it

Earlier this weekend, I went on a stamina-testing four dates in 24 hours:  dinner and live music on Friday, followed by coffee, lunch and dinner on Saturday. I also managed to squeeze in a weekend haircut, brow wax, girlfriend’s birthday celebration, yoga class and some other miscellaneous errands and chores.

As you know, I’d already begun to question why on earth I’m doing all this. Even before my first date of the weekend, I’d begun to realize that I’m no longer sure what I want out of this; I only know that I haven’t yet found it. And maybe, once again, I’m realizing that I may not be ready to find it.

But I suppose, as far as you, the reader, are concerned, all of that contemplation is neither here nor there…so, let’s get on to the recap:

  • Friday night dinner and music with the legal eagle was pleasant. This was the fourth time we’ve met and, to me, the pressure was on to either find a connection or cut him loose. We’d had many pleasant conversations, especially over the phone, and there are many things to like about his personality…but I simply couldn’t find myself drawn to him physically. He was too awkward to make a move, and I (for whatever reason) just didn’t have it in me to take some action that might invite or welcome his advances. Again, he showed up with a series of small gifts, some of which were thoughtful, others cheesy. As you know, I love receiving gifts, and his explanations for what and why he chose were enlightening. Conversation was engaging and I felt entirely comfortable being exactly as I am, unfiltered. So why couldn’t I get excited about him? Truth is, I don’t know. Yet the humor is always in the superficial things we notice that turn us off; they may not be enough to kill a deal by themselves, but they can add up. So, here it is:  he dresses like he’s from some outer-ring suburb (which he is), a little shlubby — black tee-shirt and trousers with an ill-fitting button-up shirt over the top — all matched with the sort of casual brown shoes you’d see in a Land’s End-type catalog. Not the sort of dinner and drinks downtown combo you’d expect to see in a nice downtown club. Then, while he generously picked up dinner and drinks, I stole a glance and found him to be — in my mind — a less-than-generous tipper (I like to stay in the 18-20% neighborhood myself). Finally, I was relieved to be able to watch the musicians on stage during our meal, in order to avoid gazing the caveman-like spectacle going on in front of me. He was hunkered over his meal as though eating was, at that moment, a serious job, ripping into it with fork and fingers. And it’s not the first time I’d noticed less-than-pleasant table manners and poor tipping — things that, over time, would grow to irritation. In the end, I told him how much I’d enjoyed our conversations and that, having tried to feel something more, I just didn’t feel any attraction.
  • Date two:  Saturday morning coffee. I had to be cordial, because the fellow across the table from me has a child at the same school and in the same grade as one of mine; we are likely to run into each other at school functions. But, truth be told, he was so negative, so whiny, so bitter, that I couldn’t get out of the conversation fast enough! Largely because I couldn’t get a word in edgewise. Turns out, he moved out less than a month ago…and I’m guessing those feelings are just too raw. Rather than intellectualize any of these dates, I’m simply trusting my feelings. And my feelings were that I just wanted to get as far away from him as possible!
  • Date three:  First meeting with a pleasant, thoughtful gentleman. Met him on a lovely patio for lunch. He was a good conversationalist, nice, honest about his height (about as tall as I am — which, by itself, is not a deal-breaker). His voice and speech patterns reminded me of someone, someone I like — and I finally realized that it’s my former brother-in-law, a mensch and a nebbish. Again, no magic. Alas, as we got up to leave the cafe, I noticed that the khaki walking / cargo shorts he was wearing had an elastic waistband. Enough said. I have no way to appropriately articulate to a man what might be wrong with such a choice; the gulf between our worlds is simply too wide.
  • Date four:  Second date with a digital guy, sushi. I hate that he most certainly weighs less than I do (yes, insecurity rears its ugly head). He is slightly taller than I am, dresses stylishly, has some Jim Carrey-like goofy looks, dresses well and told me stories that highlight the importance he places on parenting his daughter. He also confessed to having gone shoe shopping with a gay friend — which clearly means that he has both tolerance and patience. Ultimately, he has lived on his own for nearly a year, but his divorce proceedings drag on…I get the feeling he’s not going to put the moves on me anytime soon, because he has a pretty conservative view of right and wrong. So I like that he’s in no hurry, and I like that we spent a great percentage of our time together laughing. Am I crazy about him? Not yet. Do I want to take him home and tear off his clothes? Not yet. But this one I will likely see again.

In the end, my weekend delivered a few revelations and one clear winner…who is not in a place to develop a deep and committed relationship. And maybe, given my ambivalence, that’s just fine for now.

About failedatforty


7 responses to “not sure what I’m looking for; only know that I haven’t found it

  • A Dog With Fleas

    I laughed out loud about the man with the elastic waistband!! Definitely a deal breaker in my book too. What man would wear that out on a date….espeically a first date!! Your last date sounds like he has great potential. And you have a great attitude towards all of this. Can’t wait to hear how it goes with him. Good luck and have fun!

    • failedatforty

      Thank you! I am so pleased that you understand, with no further explanation, just how wrong that elastic waistband was…just one step away from Sans-a-belts! Nothing could make me happier than to hear I’ve given the gift of laughter. ;-)

  • Suzi Shumaker

    Wow … you’re a busy lady. Thanks again for letting us readers live vicariously through you.

  • terrid614

    i love this story. good lucky in your dating endeavors. after reading this i now, recognize why i am content to sit at home on a saturday night. am i too picky? maybe. am i perfect? certainly not! i just have high standards and all of those things you mention definitely would be deal breakers: hello elastic pants man. i also could not agree with you more regarding the tipping……you made a lot of valid points! none of these guys are your happily ever afters…..at least in my opinion! best of luck! i give you a lot of credit for putting yourself out there! xo

  • you’re doing it wrong! « failedatforty

    [...] on my recent girls’ weekend, I shared a few of my dating-gone-awry stories — you know, like the guy with the elastic waistband, the guy wearing those hideous brown [...]

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