In Over My Head

Scanning the pictures of guy after guy online in strangely addicting. I was back in the saddle, swiping on my phone, seeking anyone with potential.

I was PB (post-Belgian), and found myself texting an Oregonian who recently relocated to Sarasota. We texted back and forth, and made a plan to meet last Sunday on Siesta Key.

Oregon Guy was a golf pro for many years and is a musician. We connected initially because he was only the second guy I met online who was a fan of the same kind of music as me. We had a lot in common. So much so, that it made me think of that Seinfeld episode where Jerry meets someone exactly like him, and they fall for each other immediately.   By the end of the episode, they hate each other for the same reason.

We spent several hours talking, and I found myself divulging gory details about myself that will not only never be disclosed on this blog, but won’t be disclosed anywhere. I heard myself saying several times, “what the f#$%, I might as well tell you.” And, to my surprise, it not only didn’t faze him, but he seemed genuinely interested.

By the end of the day, we agreed to start off as friends and see how it went.

After I got home, I received a text from Oregon Guy saying he had a great time, and I said the same. A little while later, I got a text from someone else.

“I miss you.” It was the Belgian. I told him I missed him too and the next thing I knew, he declared that he would be waiting in the empty parking lot of a restaurant we had gone to. I told him, no, please don’t. But he said that yes, he was going to be there. If I was honest with myself, I had to admit I was flattered by the gesture. So, yes, I buckled and met him close to 11pm on a Sunday night.

I explained I was seeing other people, and that I would not be rushed into anything.  He said he was “fine” with that. He still wanted to see me. Since we are so good at parking lot make-out sessions, we continued along that path. The next thing I know, I’m back to seeing the Belgian again.

This song is dedicated to Oregon Guy, who took me to see these amazing guys this week. Oregon Guy is tall. The band is called “Tall Heights.”

I think I’m in over my head.





Dazed and Confused

When I go out on a date for the first time, I do my best to listen, and focus on this brand new person sitting across from me.  Simultaneously, my brain is firing a list of questions.  “Am I ok with his big fluffy hair?”  “Does he notice the makeup-disguised bags under my eyes?”  “Does he think I’m funny?” “Do I think he’s funny?”  I do my best to snap myself back into the moment, and go into “learner” mode (a nod to a book I’m reading) vs. “judger” mode.

The Belgian and I dated for just over 3 weeks, one of which I was out of the country.  By any measure, not long.   He was smart and quirky (liked), talked a lot about his vision and philosophy (didn’t like), good looking and tall, (yup, liked), ambitious (liked), slept in a gauzy-curtained canopy bed (uh, wasn’t sure what to do with that one), and wanted to be in a relationship right away (did not like).

My feelings for him were a giant bucket of confusion.  We were in communication pretty much every day, but what we actually talked about I couldn’t say.  We kissed considerably and we kissed well.  I never imagined myself with someone like him, but I did find his ridiculously sunny outlook endearing.  His ability to communicate was hampered by his lack of command of the English language, which, in turn, fired my brain to color in whatever I wanted him to be.

After Thanksgiving and my trip to Norway, I found myself in his apartment and in his arms.  And more confused than ever.  Over the next few days, we both were preoccupied.  The next thing I know, I’m getting a text, written at midnight, asking me what the problem was.  Huh?  I didn’t know there was a problem.  The following day I received a long text saying “he was confused about our relationship, didn’t know what I wanted, wasn’t sure if he was the right man for me…”  The thing I admired the most about The Belgian was the same thing that was coming back to bite me.  He was unapologetic about putting his feelings out there, and I, subsequently, became enamored with all his enamoring.

But now he was forcing my hand, and after just three weeks, I had to admit, it was just too much too soon.  I told him I liked him, but that I didn’t think we wanted the same things.  I’m sad.  I will really miss The Belgian.

Back online.  A few swipes right, I’m off to another meet and greet, and another Head Full of Doubt.





Yesterday is Here

I started online dating a few years ago, and this is the story of one of the first guys I met.

His profile said something funny about his considerable eyebrows, which made him stand out among the hordes of men who think women are attracted to big fish, cars, and photos of them allegedly being worshiped by young, busty waitresses.  Eyebrow Guy and I started to text occasionally, but it never went anywhere.  In the meantime, I became the victim of an alien abduction (my only explanation) when I met Disney Guy, who taught me, by way of demonstration, the meaning of ghosting.  My heart was broken.  On the heels of this, Eyebrow Guy popped up and we decided to meet.

I spotted him sitting outside with a library book as dense as Atlas Shrugged, a book I hated and still resent having spent so many months of my life reading. He suggested we go next door to a restaurant and get a drink, which progressed to appetizers and the obligatory life story conversation.  He described his life as a struggling artist in New York City. That’s one of the best things about dating.  Even if it doesn’t turn into something, I dig when someone opens up their heart.  That feeling of connection is truly life giving.

We went on a breakfast date that was followed by us going to a used bookstore. He immediately wandered off, and I didn’t quite know what to do, so I wandered off myself.  It was strange, but I was oddly drawn to his quirkiness.  When it was time to leave, I stood on the sidewalk, amidst a cold wind, and wondered if he would kiss me goodbye.  He didn’t, but he did ask me for dinner the following week.  He wanted to cook for me, and I agreed.

A few days later, he asked me my food preferences, which struck me as very thoughtful.  I was feeling more intrigued by him.  Saturday morning rolls around, my phone is ringing.  It’s a number I don’t recognize, so I ignore it.  Then, I get a text.  It’s Eyebrow Guy’s sister, and would I please call?  This made me uneasy, but I went ahead and called.  On the other end was a woman I’ve never spoken to, crying, telling me that her brother was found dead last night. She found my number in his phone, and wanted to let me know. I’m stunned.  He was just a few years older than me, and didn’t seem at all unhealthy.  She told me that he had complained of chest pains a few days before, and apparently dismissed it as indigestion.  I told her I was so very sorry, and we said our goodbyes.

I took a break from dating after that.

This song is dedicated to Eyebrow Guy, who I didn’t know very well, but I’m guessing would approve of Tom Waits.


I think I’m starting to like The Belgian.  I suppose this is the goal.  But, once feelings begin to enter the picture, well, let’s just say the picture goes from light and breezy to dark and twisted.  In other words, my head and my heart begin to war with one another.  I don’t like this.  At all.

After Friday’s muddy make out session, we made plans to see each other Sunday, but it never happened.  My phone died, and I couldn’t reach him until later that night, when I finally came up with the idea to message him on LinkedIn. He wasn’t at all bothered that I didn’t get a hold of him. I expressed that I would have been upset if the situation were reversed.  He said he just figured I had something else to do.   Am I dating a robot?  I’ve been watching Westworld; maybe The Belgian is a “Host.”

We meet for dinner Tuesday night, and he kisses me softly when I meet him.  I’m slowly starting to melt, which translates into me beginning to freak out.  It’s easy to date when I’m in the role of innocent bystander.  Now, suddenly, I’m part of the show.

We talk about things on our ‘bucket list,’ and he tells me he wants to buy a sailboat.  Sailing is one of those things that’s perpetually on my list, but I’ve never quite found the time or the energy to commit to.  He wants to sail to the Keys, and maybe I can go with him…?  He then asks where I’d like to be in five years.  Am I on a job interview? I’ve never been much of a planner, and I can tell he is.  But he also seems to be able to get things done, which I find appealing.

We share similar interests, but I’m still not entirely at ease in his presence.  What to do with all that uncertainty? As we sit across from one another at the table, he reaches out and takes my hands into his.  This makes me think of a friend, who asks me periodically if I’ve met “Mr. Hand Holder” yet? (I’ve expressed to my friend that I’m not only looking for someone to have sex with, but who also wants to hold my hand).

Maybe I have…

This week’s song, totally unrelated to the post, is dedicated to my friend, confidante and fellow concert kid Chuck, who accompanied me to see the Drive-By Truckers this week.  On second thought, I suppose “Surrender Under Protest” may suit the post after all.


I’m Not Fine

Saturday morning.  I don’t want to get up, so I don’t.  Who needs yoga?  I’m engaged in meaningful discourse with random strangers I meet on dating sites.  Surely this is the best use of my time.  Today, I’m texting back and forth with The European, and he asks if I want to meet that day.

He’s good looking and dressed strategically hip.  I later learn he has a model friend in Europe who picks out his clothes.  He’s Belgian and his English is a work in progress.  I don’t talk much, and when I do, I make jokes, so I’m down to nearly zero material.  I listen to him talk about his life philosophy and vision and priorities.   I guess this matters, but can’t we talk about something else, like the flavor of toothpaste we like?  Truth be told, many of our interests and ideals are aligned.

He calls me the next day, and we make plans to meet Wednesday night.  Wednesday morning arrives, and like many others, I’m bewildered, shocked and sad.  I stumble through the day, and despite my mood, decide, what the hell, I’m hungry, and since he’s yet another guy that talks on autopilot, I’ll go and at least be distracted from my dispirited thoughts.

He’s smiling.  He smiles a lot, which I find a little unnerving.  Again, more talk about vision.  He says “I’m fine,” not in response to me, but to drive home the point that whatever happens during the course of the day, his response is, “I’m fine.”  Can I really be with someone like this?  I’m the person who watches sad movies and listens to sad songs, because I really, really like them.  Another refrain of his, “no problem.” No problem, no problem, no problem.  In my mind, that is starting to become a problem.

After dinner, he walks me to my car, and his kiss is what stirs my interest.  I don’t know what to say to this guy, but I do know how to kiss him.

Friday night, and yup, another Tiki Bar. I’m having an existential crisis over these Tiki Bars, but I suppose that’s a topic for a different blog.  We arrive at the same time, and he greets me and goes right in for the kiss.  And, well, the kiss is legit.  Really legit.  This is how I get into trouble.

After dinner, we amble over to the band. They aren’t that good, but I admire their heart.  He asks me to dance, and I reluctantly get up and walk over to the brightly lit, sandy dance area that is unoccupied other than us.  We start to dance, he tells me he has no rhythm, and walks off.  What?  I look up at the band and make the same gesture my son used to when he disagreed with a ref – that “I can’t believe you just made that call” gesture.  I decide to stick it out anyway, so there I was, on the dance sand, rocking it out until the end of the song.   When I got back to my seat, I told him I was ready to leave.

Which was followed by a very, very long goodbye in the parking lot.  It ended when the tide rolled in and we were standing there, two 50 year olds, acting like teenagers, kissing with our feet stuck in the wet sand.  Is there a metaphor in there somewhere?

Two songs. I just really needed Frank Turner this week, and well, the second one is self-explanatory.



Alright and Not Alright Guys

This week, I turned 52 and had encounters with 5 different guys.  Here’s the highlight reel:

  1.  Pack a Bag Guy

Disturbingly beautiful blue eyes, a voice that made me melt, and from what I could tell, a reformed bad boy.  While he’s talking, I’m imaging cuddling on the couch together, having pillow fights and lots of kissing.  I snapped myself back and listened to his stories of growing up in LA, like the one about his stint at a roller skating rink that Cher rented out weekly for private parties with celebrities in the 70s (complete with bowls of Quaaludes, of course).  He became a hair stylist for the same reason many guys play guitar (the chicks) and moved to Boston to open a salon.  To which, predictably, he progressed to becoming a bodyguard and a state deputy, and ultimately, a private investigator. I really had no sense of who this guy was, and didn’t give a shit.  I was attracted.  We ended the date with a sweet kiss, to which I received a text afterwards indicating that he thought I was “yummy.”  I gathered he wasn’t referring to my soul.  He followed up by suggesting a date next Friday that would entail dinner and breakfast, and that I would need to “pack a bag.”  I countered by suggesting he come to visit me instead of meeting in the middle (we live a few hours away) and that he would NOT need to pack a bag.  After a few failed attempts at compromise, my reply was to not reply.

  1. Update on Concert Guy

Text from me.  “Hi.  Just checking in.  Are we still on for tomorrow?”  His reply.  “Hey.  I’ve got to be honest.  I’ve started seeing someone.  I guess we waited too long.”  I wished him well.  Admittedly, my ego was bruised, but, we really weren’t a match.  Hopefully she likes “badass” 70s rock bands.

  1. Not a Motorcycle Guy

Sunday at noon, the Tiki bar scene of two previous dates.  We walk in and pass rows of motorcycles, and I ask if he’s into them.  He quickly and affirmatively answered “NO.”  Soon after we took our places at the bar and exchanged information about ourselves.  He lives on Siesta Key, the scene of my mostly lawful adolescence.  I enthusiastically shared my experience at the drum circle there a few weekends back.  His reply, yeah, the drum circle is “definitely DIFFERENT.”  My bohemian alter ego felt slighted.  When one of his sentences started with “not to be negative, but…,” I knew this would never work.  He must have sensed my unease, so he stopped the conversation, said that obviously it was up to me if I wanted to see him again.  I sensed a tinge of resentment, like he was planning for me to choose the alternative option.  I did.

  1. Patch Guy

After a few dates, I had to admit, I didn’t see us being anything more than friends.  His response, “oh well, you win some, you lose some.” He is nice, respectful, and we both love going to listen to the same kind of music (his take on the Jason Isbell show, “amazing”).  He restores old motorcycles as a second business, is easy to be with, and wears an eyepatch. I’ve made a new friend.  Sunday night, we went to a funky live outdoor music venue, where he introduced me to Todd Snider, and we had a great time.  He’s definitely, definitely, an Alright Guy.

  1. Drunk Guy

7:48 pm.  I accept the reality that I’ve been stood up.  I’m starving, so I pony up to the bar, order food to go, when I receive a text.  “You still there?”  I tell him I am.  A few minutes later, I spot a guy, slowly, slowly, inching his way, Frankenstein style, to the bar.  He spots me, stands next to me at the bar, and unintelligibly mumbles something.  He looks me over, his eyes linger at my chest, and says, “I fucked up.”  “Yup, you did.”

This song is dedicated to my friend Patch Guy, who turned me onto Todd Snider, and is one Alright Guy.


Not Giving Up

Bonefish.  Friday night.  Another meet and greet.  He offered me a drink, I ordered a club soda, and he asked if I was Mary Poppins.  I assured him that I was the furthest thing from Mary Poppins, to which he simply shrugged.  His body language seemed more appropriate for sitting on a bench waiting for a bus than being on a date.  He had a weariness about him, like, why bother trying.  But I dug in my heels, pulled out my sassy side, and he started to warm up a bit.

I learned he was born in Puerto Rico to Cuban parents, went to college in the Midwest and spent some time in San Francisco before moving to Montana.   His description of himself:  investor, black sheep, surfer, pharmaceutical rep, snowboarder, Trump supporter.  Uh oh.  He said he was a hippie then “everything changed” when he moved to Montana.  The better part of me should have asked what changed, but, frankly, I was enjoying myself, and intuitively knew it was only going to go south from there.  He accused me of being judgmental when I told him the Trump thing was a deal breaker, to which I admitted, was probably true.

We both got quiet, and sure enough, out came the wallet and the signal to pay the bill.  I wasn’t sure how much hostility I was dealing with, so I offered to buy my club soda and coffee, which he said was ridiculous.  My response, “well, I felt like things took a nosedive.”  Maybe my bluntness surprised him, but he cracked a smile.  I suggested we go outside and duke it out.  He laughed.  Once outside, he lit up a cigarette and I got into my best boxing stance.

He texted me later and said some very nice things and offered to be available for anything I wanted, whether it was comedy, tragedy or romance.  He seemed so jaded in person that his words surprised me.  I said thank you, but I knew that was going to be that.

Next week:  BOGO.  Pack a Bag Guy and the Pessimistic Sales Guy