The Dating Misadventures of a Single Mom

It was a gorgeous summer Friday and I was leaving work on time no matter what.  I had made plans to meet friends at a trendy bar to hear some local bands show their stuff.  My stomach felt that excitement I remembered from my college days – when you just went out, feeling carefree, not knowing exactly what the evening would bring – but you couldn’t wait for it all to start happening anyway.

As part of my pampering ritual, I treated myself to another night of 80’s music, a long and luxurious bath, and took my time getting dolled up.  Maybe Prince Charming had heard about the bands too?  And we would gaze into each other’s eyes? And know we had found each other?  It could happen.  Or so I’d heard.

My friends and I arrived at the club just in time to get some seats and I settled right in. More friends of friends arrived and soon, my girlfriends were up and about chatting, and I was sitting at the table alone, enjoying the music. It just felt so good to be relaxing, hearing familiar and unfamiliar voices chatting happily, listening to music, and not thinking about anything in particular.

As my cohort of friends shifted, grew, co-mingled, and coupled up, two guys ended up talking right behind my chair and one of them kept bumping into my chair as he spoke. At about bump three, I turned to look at whose caboose was brushing and nudging my chair, and the owner of the caboose turned towards me too.  Immediately my face felt hot and I had no idea what to say; he had huge, melty brown eyes.  Why had I turned around?!  Mr. Caboose immediately delivered a warm smile and an apology for the chair bumping. I smiled back and said it was fine, and turned back to the bands quickly, embarrassed but not knowing why.  He was mighty cute.  And I was…definitely 16 years old again.  A minute later, a waitress happened to walk by and he stopped her and then asked me what he could get me as an apology for the chair-bumping.  It was very sweet and…well, “charming;” did I mention a Prince?  My smile got bigger.

The drink came and as he was fishing into his wallet for some cash, his friend, Art, sat down on one side of me and started chatting.  Mr. Caboose, (aka Wes), came over and sat in the chair on my other side and soon the three of us were talking and laughing and screaming silly things to each other over the music.  No part of our conversation was thought-provoking or deep – it was just random, unabridged commentary on the music, how the band members looked, and how wonderful our summer had been so far.  I was having so much fun talking about nothing.

Soon the bands took a break, and we started talking again.  But a few minutes into it, something changed noticeably.  Wes would bring up a topic and Art would quickly take it over and explain how much more he knew about it.  Or Art would start talking about something and Wes would say something about how a girl wouldn’t really be interested in hearing about such and such, and then change the topic.  Oh my goodness, I thought, two grown men were actually competing for my attention in some primitive and petty way!  I ate it up – nothing builds self esteem like having some guys (who you don’t even know) compete for you (even though they don’t know you) when you are in your late-30’s and recently divorced.   I mean n-o-t-h-i-n-g.

I had no idea if either of them was a “match” for me; in fact I knew very little about either of them – but I was enjoying the attention thoroughly.  Wes had caught my eye right off the bat with his warm smile (and his…er…caboose) – so I admit I leaned a little closer his way based on nothing but his good teeth and his ability to casually bump into me with his backside.

Things escalated a bit when Art’s ride came over to say he was leaving soon;  Art and Wes actually started cutting each other off as I listened to the music.  It was immature and silly; clearly, they were 16 years old too.  I didn’t care.

Our undefined group of three was going to break up soon but I didn’t know quite how; I felt the curiosity of attending a new high school on Day One: kind of excited, kind of worried, kind of uncertain.   As Art’s ride started to walk out, Wes put his hand firmly on my thigh and said “ok Art, see you later man.” Despite the fact that his movement had nothing to do with my thigh and everything to do with him and Art – the objective observer in me was impressed by Wes’ smooth, Fonzie-like maneuver.  Art left with a polite goodbye.

This world was so interesting to me.  I was entering another phase of learning: “Single working mom dates again and remains baffled yet inexplicably attracted by immaturity of opposite sex.”

At the end of the evening, Wes asked for my number and I gave it to him.  Well that was simple, I thought.  Everyone had made the boy-will-call-girl thing sound so difficult and anxiety inducing.  It had been fine.  I went home smiling.

Naturally, I did the play-by-play-replay with my girlfriends the next morning. However, that whole Saturday went by with no calls.  I had only checked my cell phone 100 times or so.  I also checked and re-checked my home voicemail – even though that wasn’t the number I gave him!  So strange, I thought, when he said he would call.  Maybe he was at a family event all day?  Sunday came, no call. I was slightly annoyed now; what had been the point of the mini-competition if he wasn’t going to call?  Monday came and I kept looking at my phone through meetings and conference calls (predictably, I called myself to make sure my cell was working).

That night, I called a girlfriend who explained it may take a week to get a call from Wes – if I ever got one.   WHAT??!! I thought.  How do people live through this?  This was so nerve-wracking and yes, it was anxiety-inducing – and I didn’t even know if I liked Wes!

Thankfully I didn’t implode because he called me the next day and asked me out for drinks on Friday – and I said yes.  We made plans to meet at a trendy outdoor bar in Lincoln Park and I was back to that school-girl-gets-asked-to–prom feeling.  Back to my closet for something to wear, back to my mirror to figure out my hair.  I had a smile on my face all week.  I laid out my outfit that Friday morning before I went to work, figuring I’d have just enough time to change and then go out for a drink that could maybe turn into dinner, which could maybe turn into a relationship, which could…?

Unfortunately, my reality and my imagination were in two different, perpendicular universes: my work day got away from me and I ended up having to go straight to the bar from work.  Not ideal, but ok.  I went to the ladies room.  I still looked together in my work clothes– though a bit tired and, well, official.  I put on a fresh coat of my new “luscious” lip gloss and fluffed my hair with my fingers.  Then panic snuck in as I wondered what we would talk about? I didn’t know him well enough to know which topics were ‘good’ ones and which topics were ‘bad’ ones.  I was so rusty at this; what if he didn’t like me?  I really preferred to be liked.

I managed to arrive at our designated meeting place within five minutes of our meeting time.  Wes was at a table already (whew) so I walked over and we said our hellos.  It was a beautiful sunny afternoon in with a light breeze – absolutely perfect for a romance, I thought.  We ordered our drinks, and Wes started to shift around in his chair, like it was suddenly filled with pins and needles.  He was looking all over the place, just not at me.  Maybe he’s very shy I thought; still, self consciousness slipped into me every time I took a breath.  We needed some conversation, I thought.  I plunged in with a few getting-to-know-you questions: what do you do for a living (he had just quit his job and was earning money temporarily serving papers to people who were being summoned by the courts);  hmmmm, I thought, not your everyday job, what else can I ask…?;  how many siblings do you have (one);  maybe he didn’t get along with the sibling so he was short on this reply?;  where did you grow up (here).  Sigh.  After all those questions, I really didn’t know him any better.  Further, Wes appeared to have no curiosity about me as he asked me no questions.  Was he uninterested or was he disinterested, I pondered, being very intellectual and above it all.

Bit by bit, our conversation stuttered and stumbled like a drunken sailor.  My stomach felt that sinking feeling again. I sat back and pretended to enjoy the evening sun for a few moments.  My mind raced with advice: this wasn’t too much fun and I should have stayed on my couch, I am not cut out for this, I feel so tired all over and I need to get home, I need Thai food and ice cream. As I gazed everywhere but at Wes, he suddenly posed a question.

Wes: “Do you like motorcycles?”

Me, relieved, smiling: “Well I have ridden on them and it was exhilarating; but only with the right gear because I’ve never broken anything and I want to keep it that way! Do you like them?”

Wes: “I don’t know anything about them and I’ve never ridden one.”

Silence.

Wes: “Do you like volleyball?”

Me: “ I like watching it at North Avenue beach in the summer;  and I saw the Olympic teams play in Atlanta in 1996; I’m not too good at playing it though. Do you enjoy it?”

Wes: “I don’t know. I’ve never tried it.”

Me: Wishing we were listening to a band again.

As this line of questions continued, I marveled at Wes’ ability to raise only topics he knew nothing about and then wait for me to chime with what I knew, and then ask him if he liked that hobby/country/restaurant/scientific discovery he raised…only to hear, “I don’t know. I never heard/saw/visited/read anything about it.”

I was pretty certain that Wes did not like me.

I had no idea what to think of him.   And I felt so deflated – I had looked forward to this evening all week.   A slow,  dull, lingering throb began in my head as I focused on getting through my drink.

As soon as I finished my last sip, I thanked him for the drink and started to get up.  Wes got up too and then surprised me by offering to walk me back to my place.  At least he’s polite, I thought.  So we strolled a few blocks and then I stopped about half a block short of my building: my ex was unexpectedly sitting in his car in the driveway of my apartment building, with my daughter!  Immediately, the exhaustion of the last year and a half came back to me like a 50 foot wave. I wanted to lie down.  I needed to sleep.  Where was my couch?  Why were they waiting there?

I told Wes that my ex was sitting there  – and we said an awkward goodbye mid-block (note, this is pretty much how not to end a date).  As I was about to turn away, Wes said he’d like to see me again.  I was so very surprised as my mind was rapidly shifting back and forth from single-girl-dating mode to mommy-mode.   I could see the bouncy head of my little bundle of joy and energy a half a block away… did Wes like me?  My body was absorbing currents of anxiety like I was a parched sea sponge…or was Wes just being nice?  Was I about to have another fight with my ex?  Maybe Wes was just nervous?

So, I said what anyone in my position would have: “Thanks Wes, I would love to.”  I got back to my driveway, took my daughter and asked for no explanation (and none was offered) as to why they were waiting there.   Lovely.

I went upstairs and got my daughter settled, poured a glass of wine, and then called a girlfriend.  I heard a resounding: “Anyone can have a bad first date; give him a second chance.” I agreed – and the night with the band had been fun.  I also received the girlfriend-to-girlfriend-verbal-hot-fudge-sundae that we so generously bestow upon each other: “you’re pretty, smart, and successful; you can be a formidable woman; you have so much going for you; he was so, so intimidated by you.”  It worked, as always.  I felt optimistic again.  He must just be very shy.  And talking during a band was very different from talking at a bar.  Plus he was so cute!

As I got into bed that night, I decided that I was a modern woman and I was not going to sit around waiting for the phone to ring – I was going to leave him a message tomorrow and ask him out.  Why not?  I had never done this before, take initiative when it came to a man; but this was the new me.

True to my word, I found some time the next day, when my daughter was napping. I buzzed through the calendar in my blackberry to find an evening when I wasn’t traveling for work, when I didn’t have my daughter, and I didn’t have a conference call with someone in China/Europe/US at the crack of dawn the next day; finally, I found a date that looked clear, and a smile spread across my face.  I left him a voicemail quickly, before I lost my nerve.

“Hi Wes.  This is Swati.  Thanks again for the drink yesterday.  It was nice seeing you.  Sorry about the, umm…non-traditional goodbye (small , nervous laugh).  Let me know if you’d like to go to a movie with me on July 17th.  We can grab a bite too if you’d like.  Talk to you later. Bye!”  I sounded pretty good, not too many “umms’ or pauses… casual and confident.  I was pleased with myself.  I hung up…what a relief!   I better go in and put a ‘hold’ on the evening in my calendar, I thought.   I looked back at my blackberry and paused in horror: I had just asked Wes out for an evening 6 weeks in the future!   I was mortified!  Good grief!

I never heard from him and we never went out again.  And I am pretty sure that’s fine.

(This is a story from my past dating misadventures…originally written for my book but now on the cutting room floor…I couldn’t resist sharing!)

Tags: dates, dating, dating misadventures, mommy, Prince Charming, single girl dating, single mom, single working mom