Singledom Unknown

I roll over in bed this morning, still half asleep, and instinctively throw my arm to the other side. There was no one there. Suddenly, I shoot straight up, wide awake. There has been someone on the other side of the bed for decades, but not today… today there is only me. The realization that nobody was there dawns on me, as it usually did in the mornings. Old habits die hard, I guess.


But on this morning in particular, someone is there… I can feel it. I look at the clock, it’s 4:12 AM. I sit up, rub my eyes, put on my glasses, and as focus arrives, I stand up and walk out into my dark living room.


My fake fireplace is on, casting a dark orange glow across the room. In my sleepy haze, I see a person sitting in the chair in the corner. Startled, I can’t make out who it is, just a fuzzy silhouette; but I live alone so this is not good. I decide to play it cool; I could still be dreaming after all. As I scan for something I can use as a weapon, the silhouette says, “Hello Steve.” in a voice I do not recognize. I cannot even discern if it’s male or female. “What do you want!” I say, my voice a couple of octaves higher than normal. “To welcome you to Singledom, I am your guide,” says the silhouette, putting down a cup of coffee on the side table, that he/she obviously helped their self to. I am oddly reminded of the ghosts from A Christmas Carol. Was I even talking to a person? I assume this must be a dream; can’t die from a dream. I decide to play along and see where my mind is taking me.


“So, what’s your name?” I ask.


The silhouette responds, “You can call me Pat.” Of course, still no idea if male or female.


“Okay ‘Pat’”— I say snidely—"I have to tell you right up front, I’m pretty convinced the online dating scene is hopelessly broken, so I can hardly wait to hear what kind of guidance are you going to give me for Singledom?”


“Why, how to get out of here, of course!” Pat says.


I ponder this, and say, maybe a little challengingly “How do you know I won’t like it here?” I’m already “testing” Pat.


“We have an extensive file on you”—Pat shakes a folder in the air— “we know”.


Caught off-guard by the file, I say “But I have never been single, it seems like there could be some upside.” Who was I trying to convince? Pat? Or me?


Pat replies, “For some men that is probably true, but you are not one of those men Steve, for you it will be all downside. Can we get started now?”.


I think for a second, trying to decide if this is a complete waste of my time, and say “Ok sure… why not?” I mean, I’m single… I have the time to waste.


Pat begins “I am going to ask you a few of questions to see what I am working with here. You need to answer honestly, or I won’t be able to help you get out of here. Are you ready?”


“Hit me with your best shot” I say, this was certainly a more interesting way to begin a typically mundane morning.


“Okay, first question”—Pat leans in and pauses—"are you an asshole?”.


“What!”—I say incredulously— “That’s a pretty stupid question to start with, I am obviously NOT an asshole.” I was shocked at his/her audacity to even ask that.


Pat responds, “It may be obvious to you, but not to the one who may lift you out of here, who by now, may be assuming that all men are assholes”.


Ugh, I drop into the chair across from Pat. I had not thought about that at all. Maybe Pat is not an idiot after all.


“It looks a lot different from the other side Steve”, Pat explains, “The one who will pull you out of here may get 100’s or 1,000’s of likes a day.”


“What! I get like 10… a week!”—I say shaking my head— “Is my profile really that bad?”


Pat goes on, “It’s the way it is, women get 50-500 times as many likes as men, mainly because women are much pickier in Singled

It's fucking 4:00 on a Friday, and I have no plans for the evening. This blows. Not unusual, I have had several "nothing to do" Fridays since I became single. I have many friends around the world, but none local really. The few I had here, were my exe's friends spouses, which I lost in the divorce along with the dog.


Sometimes, friends visit. Microsoft has a local training facility that often brings them to town and we'll hang out. We'll hit a few bars, have a few drinks and have a great time. Bars can be fun, I'm gonna go anyway, by myself and check it out. I mean this is how people met before online dating right?


4:30, time for a shower. As part of my transition to Singledom, I replaced my entire wardrobe. It started with a pair of $800 Salvatore Ferragamo shoes. I walked in and out of Neiman Marcus four times before I rationalized that I deserved them. It's amazing what a pair of shoes can lead to. I finally understand why women love shoes... it creates a need to buy clothes to go with them.


Imagining my coming evening, I carefully select an outfit from my growing wardrobe of designers, many of whom I have never heard of. I have my limits. I bought a great looking black leather jacket from Armani with just a small "tasteful" insignia on the front pocket. It was not until I got home and looked at it closer, that I saw the ARMANI EXCHANGE emblazoned across the back in 4" letters. Lesson learned, look at both sides before you buy.


Of course my outfit has to start with my brown Ferragamo loafers. I add some black skinny jeans, and a black shirt with light printed things on it... flowers maybe? I'll top it off with a brown leather jacket that I searched for to match the shoes. A spritz of YSL cologne, and I'm off. As I am riding down the elevator to the parking garage, I realize that it is not even 5 yet... fuck. No turning back now.


Sitting in my reserved parking spot, on the fourth level of the garage, is my 2019 Jeep Grand Cherokee. It's a fine car, but brings back bad memories every time I see it. It was not the car I was going to get. Still married when I bought it, my ex pitched a fit about me spending too much on a car that I seldom drive. Fuck it, I was going to get the Land Rover Velar anyway... she had a Mercedes! But on my way to the dealership, I imagined her being pissed for weeks, and rationalized that she was probably right. Instead, I turned into the Jeep dealership. We split shortly after, and now, stuck in a lease, I regret not getting the Land Rover.


As I circle my way out of the parking deck, I plug my phone into Carplay and scan my messages. Nope... nobody pinging me last minute to do something. Damn it's fucking early... but Happy Hours start soon! As I reach the garage exit, I realize that I had not thought about where to go. I pull up Yelp on my car screen to do a search. Beeeep!!! Damn, somebody trying to get out behind me, I wave and pull out to the right and pull into an empty spot on the street.


"Best Bar for Singles" I type into Yelp. It returns a bunch of clubs in Ybor for the 20 somethings. Ugh. “Best Bar for Older Singles"... same results, seriously! Damn... where have I seen single women... got it... Capital Grille at International Mall. I pull out and head off, picturing this nice bar full of gorgeous single women.


5:30. Wow, the mall is packed. I pull into the valet line and wait my turn, fully aware now that I am not in a Land Rover. "Will you be dining at Capital Grille this evening?" says the valet. "Yeah, something like that" I reply and toss him the key fob thingy.


It's still light out, but walking through the door of the restaurant I’m thrown into darkness, remembering the bar is to the left, I start heading that way as my eyes adjust. Good news, it's packed! Bad news, there is no open bar seat. As I walk the length of the bar, looking to see if anyone is cashing out, I notice that there seems to be a lot of couples. I s

I have not been out here very long; the dating scene that is. Obviously, being a rookie, I signed up for all the dating apps. I was remembering my grandfathers' motto about prescription pills... "If one is good, then three are better". He died young.


Across the dating apps, you see many of the same women, who are also exploring their app options. My friends warned me not to sign up for Tinder, so of course, I immediately signed up for it. It's definitely shady around the edges, but they are all pretty much the same... photos and limited information.


I'm not sure what you can tell about a woman from a few photos and bullet points. But you do start to learn how the "system" functions. Step one, I start "liking" a few profiles. A couple of days go by... nothing is happening. Maybe I am not doing it right, and my "likes" are not going through. I mean, I know I am a good catch. I try "liking" a few more... nothing... not even any views. This is starting to feel like a waste of time. Maybe "likes" are not enough, I add a message, "Hi!". There we go, now I am getting a few views... but no replies. I actually read the complete profile, or at least what is provided, which sometimes is not much. I decide to send a longer message, "Hi Claire, I also enjoy bike riding!" Bingo. "Hi Steve, where do you ride?"


Someone should write a tutorial for women on how to create their profiles. A single profile photo consisting of a flower, may have some important meaning, but as a guy, the meaning is lost on me. Photos of you lying in bed, or in skimpy outfits will probably get you a lot of attention, we all know men are visual beings, but I don't think most women are seeking the kind of guy who only responds to that. It feels... desperate. There is also some irony in posting a suggestive photo, and then saying "No Hook-ups". We are but men, and just not that smart.


Bullshit! Profiles are mostly bullshit. Photos from high school, weird angles, filters on every photo or no pictures of you standing. The only people who like photos of women with cutesy filters... are other women. As a guy, I don't need 20 photos either. If I see 20 photos, there is going to be one you wanted to share, maybe because it was taken at a hip place, but where you just don't look your best. I will assume you probably look no better than your worst photo. I'm not bothered by photos where your ex is cut off, it shows how you looked when you were happy with a man. Four photos is plenty, provided they are recent. Neither of us benefits from seeing how you used to look.... it's not like that is coming back.


Women seem to be more honest in their words, than their photos. Still, turnoffs for me, and I assume for most men, are statements like: "Trying this again", "My friend put me up to this", "Don't waste my time", "No Hookups", "Seeking marriage minded only", "I'll fill this in later", "Seeking that special someone (puke)". I also don't really need a detailed breakdown of who you are looking for, my profiles' job is to provide a start on that. What your detailed description of your ideal man does give us, are things we can say to you, that we know you want to hear, true or not. I would prefer to read about who you are, rather than who I should be.


Women also tend to be very specific. Height 5'-10 to 6'. Really? 2" is your full acceptable range? At the end of the day, tall/short, skinny/heavy, old/young, etc. will all be eclipsed in significance by "real" chemistry. I recently learned a new term, "sapiosexual" which is a person who finds intelligence sexually attractive or arousing.


Back to "Hi Steve!". Am I the only one who is tiring of the monotonous first dance steps?
Her, Morning: "Hi Steve!"
Me, Late Afternoon: "Hi Alexis, how are you today?"
Her, Midnight: "Great, how was your day?"
Me, Next Afternoon: "Not bad. You got any fun plans for the weekend?"
Her, 1 AM: "I might go to the beach with friends."
Me, Next Morning

I'm flipping through channels on a quiet Tuesday evening. "Hi Steve, it's Me! 😀" appears on my phone's text notifications. I open the app. Who the fuck is "Me". I don't want to be rude, but the last time I thought I could deduce who was texting me I said, "Back from your trip already?", and she said "What trip?". I am thinking that I will just stay neutral... chat about weather or something to see if she gives me a clue. But then, how awkward would it be to still not know after like two days... and then have to ask...


"Hi! Who is this?" [sent] Better not to risk it.


"It's me silly. You suggested we move to text a couple of days ago..." [received] Not helpful, a couple of days in the dating apps, is like a week in real time.


"Sorry, I have a short memory 😀 Give me a hint?" [sent] I'm hoping I don't annoy her, but I really need to know who she is.


"From Bumble..." [received] Great, now I have to go into that App and try to figure out who this is. I open Bumble and jump to the conversations tab... I see that she could be one of two. Ugh. I decide I will have to take a risk.


"Play any racquetball 🎾 this weekend?" [sent] Fingers crossed.


"No" [received] Did that mean she did not play, or she did not know what I was talking about?


"I have not done that in a while ☹️" [received] Whew, okay now I know who this is. I edit her name to "Tonya from Bumble", and go back to look at her photos again. Damn, she deleted her account, I just looked at it a minute ago, but I remember her being cute.


"What part of town are you in? I'm downtown" [sent] When I first started, I found myself in a great conversation with a girl who lived in Atlanta. I was thinking about flying up there to meet her, but then thought, how is this going to work? So I tightened up my radius to at least women I could get to... ideally in less than 20 minutes.


"I told you silly... I live on Davis Island 🤷‍♀️" [received] I am wondering if it is unusual to be having multiple conversations going on, I assumed women did also... or are they just that much better at remembering details?


"Cool! I am actually on the next island, Harbour Island" [sent]


"I know, we had this discussion... how many women are you talking to?" [received] Uhoh, this is probably not a good question.


"A few. I see you deleted your Bumble account" [sent] Maybe I can divert the conversation, because if asked specifically, I would have to tell the truth, which means I would have to go and actually count them.


"Yes, I usually only pop on there for a day or two at a time. I met you, and decided to give it a rest." [received] I am wondering how much should I read into that... but it sounds positive.


"I went back to look at your profile again, but it was gone 😦" [sent]


[incoming photo] Ah yes..... I remember her now.


"Oh yes, the cute one 😉. Since we are so close, we should meet for coffee one morning ☕" [sent] I have been down the road of a few long text conversations. Everything can seem great, then you meet, and it's just not there. I hate even thinking that having a nice conversation could end up being a "waste of our time", but the reality is, that it could well be.


"Or drinks 🍸 LOL" [received] First meetings are a critical pivot. Some women like to play it very safe, like coffee with a fixed end time since they have to go to work. I get it. I mean if things are not sparking, it sucks to have committed to a whole evening. "Drinks" is a little more aggressive than coffee, and I read that as a sign of higher interest... or she could just be an alcoholic.


"Great! How about Thursday?" [sent]


"Do you have plans for Friday yet?" [received] I usually avoid have a first meeting (I don't even call those dates) on weekends. Even if I don't have plans, it just feels like more of a commitment than "Drinks on Thursday".


"Nope, no plans. How about Jackson's?" [sent] I am n

"You make a great Manhattan." I say to the bartender, when he stops back by to ask how it is.


I recently started drinking Manhattans. It is a classic drink from way back. I discovered them this past Thanksgiving. Single now, I was asked to join my brother at my parents townhouse for dinner. My brother has been single his whole life, and has never had anything to do, other than to dote on my parents. I have always had to "fit" them into my otherwise busy family schedules, but not him... and he's a martyr about it. When I asked what I could bring, he said "nothing, I have it all covered". What a dick. But I'm not going empty-handed, and I recall my parents enjoying those classic cocktails. For Mom it was the Sidecar, and for dad... always the Manhattan. So I hit the liquor store, with my internet found recipes, to buy the necessary ingredients. Not to be completely overshadowed by my brother, I drop about $250 on high quality stuff and head over.


Dad is in rough shape, glued to a recliner, with an oxygen tank and a TV remote. He asked me once if there was something other than Netflix... because he had seen all of it. Mom looks at my armload of liquor with surprise, and my brother shakes his head and frowns. "He can't drink Steve." he says, trying to take any wind out of my sails. From the other room my Dad says, "Sure I can, it can't do any more damage." I give my brother a grin, and start following the recipes. 30 minutes later, I hand my Mom her Sidecar, and bring my Dad his Manhattan, partially blocking his view of the TV. He takes a sip, and let's out a huge smile. I have not seen him smile in a long time. I'm thinking to myself, "Fuck you brother". Then Dad hands it back to me "That was great, thanks" — Great! You took one sip. — "You can finish it" he says. So I do, and now it is my favorite drink. Dad died a week later.


It's 7:30, Thursday night at CW's Gin Joint in Downtown Tampa. This place is always crowded. I am sitting at the bar with my foot on the stool next to me, as if to say, "Don't even think about taking this chair." We were supposed to meet at 8, but I always arrive early. I enjoy my solitary Manhattan time, but just one. Drunk on a first meeting seems like a bad plan. I always find a spot where I can clearly see the front door. There is something about watching a woman, dressed to the nines, first walking in. Her face a combination of nervousness and hope, as she scans for a man who she has only seen in photos.


We are meeting for "Drinks", but of course I have a dinner reservation for 8:30 setup, in case things go well. The clock ticks 8, and as if she had been waiting outside for that exact moment, the door opens and she enters. Wow... she's the opposite of a catfish... she looks even better than her photos. I am nervous for a second that she might be out of my league... but I've never lacked confidence, and the concern passes, as I wave from my seat. Both of our profiles listed us a 5'-8", but she is wearing 4" heels, which becomes obvious when she reaches me at the bar. I don't mind a bit.


"Steve?" she says, a slight questioning in her voice. I look exactly like my profile, so I am not sure if I am detecting disappointment... but I mirror the motion, "Sarah?" "Yes!" she says, and moves in to give me a hug as I stand. I'm not sure why, but a hug seems so much more optimistic than a handshake.


"Have you been waiting long?" she says, as she drapes a sweater over her stool and slides onto it. Not wanting to seem too eager I say, "I got here just before you". She eyes my almost empty Manhattan, and obviously knows better.


We had been chatting for a few days prior, so we had already covered some of the basics. I wave the bartender over, "What can I get you miss?" he says to her. She replies, "I'll have what he's having." It does not make any sense, but for some reason, I am extremely pleased with this answer. She does not even know what it is. I'm not sure if it was

I had been eager to see Susanna again. Our first "meeting" was after work on a Tuesday, at Boca in Brandon. She works downtown, and offered to go home, "freshen up" and come back to downtown, and tempting as it was to not have to drive to Brandon, accepting that seemed like a dick move. So I picked Boca, because it was near her. That first meeting went very well, so I asked for a second "date" and she agreed to dinner on the upcoming Friday.


I'm a fan of Ocean Prime at International Mall. The food and cocktails are great. If you just show up at the bar, you would be lucky to get a table, and probably have to wait for a high top. I prefer the bar, because it has a piano player. The trick is to make the reservation on Open Table a few days in advance. The restaurant always calls to confirm, and that's when I say I want a booth in the bar. So far ,they have always accommodated. The booths are fairly large, semi-circular facing the bar, which makes for fun people-watching. Even though they can probably fit six people, I have never had an issue getting one for two. All set for Friday at 7:00 PM.


Friday, 5:00 PM "We still good?" I text her. "Absolutely, on my way home to get ready, I'm looking forward to seeing you again ☺️ ☺️ ☺️ ." she replies. I always like to arrive early for my solo Manhattan, so I shower up and start to get ready myself. She will drive herself there. It's our first "real" date, we don't know each other yet. If I were a woman, I would never get in a car with a man, until at least the fourth or fifth date, so I do not offer to pick her up.


Friday, 5:45 PM "Hey, I hate to do this last minute, but I am feeling depressed and I won't be going out tonight." she texts. Umm...weird, she was three smileys happy 45 minutes ago. But whatever, "Okay, some other time then?" I reply, as though I am not annoyed at all. I get no response.


Friday, 6:00 PM. Now what? All I was missing was the spritz of YSL, and I was going to be heading out the door! I think for a second, remembering how I hated the bar scene by myself. How much worse would that be, sitting by myself in a six person booth? Fuck it, I'll just walk down the block to Cafe Dufrain. It has a decent vibe, mostly locals; Melissa the bartender is nice, and she can make a decent Manhattan.


Saturday Noonish. "I am soooo sorry, I just had some issues last night, and I would not have been good company." she texts. I'm still a little confused, but our first meeting seemed to go so well... "No worries... I understand." I reply, even though I don't understand at all. "Try again?" she texts. Hmm, well I am not chancing another Friday night with this one, until I figure out what is going on. "How about lunch downtown Monday?" I respond, knowing she works downtown, and it would only require a scooter ride on my part to get there. "Perfect" she texts. I reply "Say 11:45, you pick a place near you?" No reply.


Monday, 9:00 AM. "Are we still on for lunch?" I text. She responds, "Absolutely, see you there!". Umm, "Where?" I reply. "Lol, how about Freshen, it's easy?" she responds. "Okay, see you at 11:45" I text. "Let me know when you're almost there, and I'll come down." she says. I'm thinking, I will fucking be there at 11:45, but I reply, "Okay 👍"


Monday, 11:35 AM. "Hey I'm almost there." I text, even though I was already there, because I am always early. "Okay, I just have to finish a couple of more papers and I'll be right there." She responds. Huh?


Monday, Noon. "I'm on my way" she texts. No explanation or apology for knowing I have been standing there, for what she thinks is 15 minutes, but was actually 25.


I see her walking down the street towards me and she waves. I wave back, and a minute later she is saying, "I was trying to get a few things done before the holiday." "Oh cool, so you are off now?" I say. "I will probably go back after lunch, I don't really have anything pressing." she says. I'm thinking, bu