the real life dating escapades of a post middle aged gay man

A few things I feel should be stated up front. In all likelihood I won’t live to be one hundred and twelve and odds are neither will you. So let us dispense with the misapprehension that anyone over fifty is middle aged. Though I consider myself sex positive (I really enjoy the company of men), I use the term ho in the urban dictionary vernacular for a bit of fun. I might choose to name myself an aging former slut but that word is highly charged and often used to make people feel bad about themselves. I never actually had sex for money in my youth though I gratefully accepted gifts from gentlemen who wanted to impress me. For the record, I would have slept with them regardless. The names of the men in this essay are changed as I would not wish to offend. Since Tinder does not have a feedback feature, I can only imagine how my dates might perceive me. This is dedicated to all the romantics who continue to go out and date even when it is often bumpy. I believe that preserving a sense of hope in this arena is essential not only for enjoying the dating experience, but because hope opens us up to a larger connection with the world and the people around us.

As I sit alone this sunny Sunday morning enjoying my second cup of coffee, Scruff is blowing up my phone with woofs. I know in my heart I should feel warmed by the attention, but I cannot bring myself to rouse. The woofs have less to do with me than the fact that a lot of guys are waking up frisky. Sunday morning is very frisky in Philadelphia, so it’s also a great time to change your profile pic. Last night I posted a new picture from my Cancun vacation taken by a local photographer and the angle is flattering (upper left). My face looks a bit skeptical and sure, it’s thirsty but I am not mad at the way my body looks. Perhaps because blue is my favorite color? Whatever the case, I am much more critical of myself (my body) than of others. Personally I adore variety. I think the world would be a sad and boring place without the endless variety men who come in all sizes and colors. A rainbow of love. Therefore every date, every hook-up has been an amazing opportunity for me to connect. I don’t always get it right. Neither do they. But it has never been dull.

When choosing between two evils, I always pick the one I’ve never tried before

For anyone not familiar with Scruff, it’s a hook up app. I mostly use it as a pro forma attempt to stay in the eye of the gay storm without actually getting off the couch. To remain visible as a sexual being within the community so that when I’m actually out I am not totally invisible. The public aspect of the profile and being seen is my main requirement. Though I go out with friends or to the occasional event, I am not really what you might call social. Myers-Briggs refers to me as INFP (introversion, intuition, feeling, perception). Basically I feel things like an introvert and I intuit the world around me as something I must responsibly engage. So in my world around the Gayborhood, as I am walking my dogs, working the store, at the bank, the grocery or in the square, I am open to being connected. At home all alone? Not so much. Which is why I also use Tinder. Tinder is my dating app. It is the tool that moves me toward going out on dates. To meet guys my age. An opportunity to try new places and meet new people. Here’s the thing.. I don’t expect to meet my next husband, I just need to get into the available pool of single men. To interact. To listen. To learn. To practice. Recently I read a book on Attachment Theory as it correlates to dating. It’s a game changer. Now that I understand how people attach, the knowledge forces me to be more aware. To see what is right in front of me. To not do what I’ve done in the past. Excuse, ignore and worry. Now I simply take it all in and listen to my first inner voice, keeping an eye out for the men who are truly secure. Secure guys are the ones I would choose as a potential mate. They not only know that they are deserving of love, they act accordingly, and treat others in kind. Anything less is about staying socially limber. With enough practice I feel at ease in the dating world, which means my dates feel at ease, which means they let down their guard, which is when things get interesting.

You only live once. If you do it correctly, once is enough

Since I want to look good on a first date without looking like I’m trying too hard, I usually wear a button shirt, jeans and old waxed suede dragon boots. I dress early so that while I am hoping he will find me appealing, I look a bit “lived in”. Unless of course we are going on a hike or something. Without an air of fuss, I want to look good and I want him to look good for me. I want the guy to want to look good for me. I don’t have many requirements or expectations but I’m always hoping that the barometer in my boxer briefs will at least roll over or react in some measure. Even at my age chemistry still counts. Some guys I meet on Tinder are chatty (read: text prone) and some are more eager to meet. Then there are loads of ghosters who disappear soon after matching. I silently thank the ghosters for not wasting my time. With Tinder I take things as they come. Life has a habit of taking us wherever it wants to go anyway. In conversation with other guys of my generation, I get a split of app lovers and those who loathe the apps vs being at the bar. Personally I see Tinder and Scruff as an opportunity to present (yeah, same as animals in nature) to a wider audience. The best advice I can give to myself before heading out the door is to be polite, be myself, and put my fantasy height requirements aside (shorter is better) while adopting a wait and see attitude. Take it one date at a time. With this in mind, I offer you a window into the last couple months of my first dates. The shade is just a bit of fun.

Sex is like playing bridge. If you don’t have a good partner, you’d better have a good hand

Drew was a sweet guy. Very nice. He fast-tracked a date to meet at a local coffee house. I was flattered. When I arrived, he was already seated. I went over to introduce myself and shake his hand but he never stood up. He never stood up. Thirty minutes into the date he told me that in every serious relationship he’s ever had the guy cheated on him. He said he attracted cheaters.

Charlie was amiable but made a fuss about only ordering local brews and was openly irritable about the selection available to our server. He then ordered and drank 3 IPAs in less than one hour at dinner. Now I don’t drink and I certainly don’t mind any guy having a beer or two but come on. Three in the first hour? I’m afraid I might have bruised Charlie’s ego when he leaned in for a kiss goodnight and got a handshake.

David showed up at the restaurant in gym shorts and a hoodie. He wasn’t coming from the gym.

Jerry found an argument in almost every subject broached over dinner. I assumed he enjoyed debating. I do not enjoy debating. Jerry was also openly bitter about his ex wife and issues regarding their finances. No dessert thank you. Just the check.

In the booth at the local pub, Matt kept asking me to taste his beer even after I told him I can’t drink. The first time I chalked it up to nerves. Second time I chalked it up to nerves. The third time...

Teddy was big man, you know what I mean? Sweet. Sexy. Made me feel all warm inside. Killer combination of short and lean. But big. God knows I tried. I gave up when my jaw locked.

Mike, well.. turns out Mike’s pictures we’re circa 2007. It all went south from there.

Hank asked about the lack of political postings on my FaceBook page. I stated my personal preferences about how I chose to interface on various social media platforms. He then began jabbering about the president halfway through breakfast and could not be moved off the subject. I think my ears started to bleed. I wanted to die. The table next to us wanted to die. Hank wanted the president to die.

Sam was a good kisser and stuff so I was happy to invite him to spend the night. He was over the legal limit and shouldn’t have driven anyway. I was a little surprised however that he brought a beer to bed. Actually, it was when he got out of bed at 3AM to go get another beer that I thought.. um, no. What the hell?

Paul wanted to talk about my marriage and why it ended. Crickets..

I had no illusions. Dating over fifty is like spending an hour or two on Mister Toad’s wild ride, the unexpected can and usually will occur. There is always a possibility for a little spark of romance, but don’t bet your retirement savings on it. Anyway, I am getting better at leaning in toward the intimacy. Especially after being naked together. I’m not running for my pants and the door concurrently anymore. Sex with a stranger is always a crapshoot, and without fail I find a majority of guys are simply looking for connection. While I want sex because.. well, you know.. I like coming, some guys use sex as the gateway to access what they really really want. To be physically close to another human being. And I get that. Profoundly. So I skirt the line between my physical needs and the idea that I am ready to be in a relationship with a great guy. What I refer to as: Intimacy PLUS. While no one ever said this was going to be easy, it is definitely worth the effort. Which is why, for the foreseeable future anyway, I will keep putting it out there. Keep dating. Dare greatly and allow myself to be vulnerable in this context. I will continue to rise to the humor and absurdity rather than feeling in any way deflated. Those little red flags my former therapist spoke about are keeping me from devoting time and energy to situations that will ultimately lead me to unhappiness. Besides, the first date stories are an endless source of amusement for my friends, and I do love to laugh with my friends. Especially at myself.