It’s been 8 years – not sure if anyone is interested or cares anymore.  I am afraid I am even more fucking clueless than ever and I may have unrealistic expectations of the dating world in my 50s.  A recent conversation with my adult son included him telling me that I would never get married or date someone seriously.  My immediate feeling of inadequacy convinced me I had to give it another shot.  My therapist was thrilled when I told her (she has been telling me to date again for years).  She described it as oppositional defiant dating and she may be right on that, but I really do want to find someone I like.  I likely never will get married or want some guy up my ass 24/7 as I have spent too much time alone and building my life this way, but having someone to do things with, someone who actually likes me but respects my boundaries and the fact that I am an introvert and need some time to myself, and is a reliable sex partner, would all be really nice.  I have a good job, my own house, am financially stable, have friends and interests, and I would like to think I am still reasonably attractive.  So, I bit the bullet and joined an online dating app again.

I had quite a few responses in the first few days – likely because I am guessing I was at the top of some new members list and showed up to a lot of users.  That interest has definitely tapered off with a few weeks of time on the app.  A disturbingly large amount of those were guys in their early to mid 20s, so clearly not age appropriate for dating. I am guessing they were trying for a cougar thing, but that doesn’t interest me at this point in my life.  A handful of them were in their 60s or even 70s, so not what I would consider age appropriate on that end either.  The app even suggested that they had found my perfect match, a 72-year-old guy who answered one of the app prompts about LGBTQ+ with, “I don’t even know what this means.”  First of all, he is only two years younger than my dad.  Secondly, why the hell would you pick that prompt if you don’t understand the question, and third, I was not attracted to him at all.  Anyway, mixed in there were a couple dozen guys in my idea of an age-appropriate range.  For the record, I have updated my profile, so I am not visible to guys at either end of the age spectrum now. 

I really tried my best with responses to anyone who liked my picture or messaged me, reading their profile and asking something related to one of their prompts or pictures.  I was not doing one word, Hey, Hi, DTF, or anything along those lines.  Most of these conversations mutually ended within a couple days or so, but I did end up talking to a couple guys off of the app.  One called me and we talked for a couple hours, mostly about books and family stuff.  We continued texting and he asked me to go out that weekend, but I had other plans, including some things with my son.  I suggested meeting Sunday for breakfast, but he said he felt like dates that were not dinners were not serious.  I offered to meet up for dinner one night during the week then, even though I would rather avoid dating on weekdays.  That Sunday night a snow storm moved in and he texted, I’m bored. DTF ?  Instant block for me.  I don’t know you, we haven’t even met, we are not on a personal level where you can suggest that either as a serious option or as a joke.  So long DTF guy.

I started going back through guys who had messaged me as the initial response was overwhelming enough that I had not responded to everyone.  I fully admit, I responded to the better looking guys first, as attraction helps.  I would be willing to bet most of the guys who had messaged me did so due to some kind of attraction, not because my prompt responses evoked some kind of instant connection for them.  I messaged a few with the same results, app conversations that mostly fizzled out, but one guy stuck (NSNG).  He suggested talking on the phone, we got along great, he was smart and funny.  NSNG asked me out for dinner for the following day.  I swallowed my considerable dread and fear – unrelated to the guy and tied to my nerves over starting this merry go round again – and agreed to the date. 

I decided to put my best foot forward for this.  I wore an expensive dress, three-inch heels, and really did my best to look good – even shaved my legs although they weren’t all that visible through my opaque tights.  When I got to the restaurant, he leaned in for a hug as I offered my hand to shake.  Then he backed off and offered his hand to shake as I leaned in for a hug.  Awkward kind of funny moment, we ended up with a quick hug and went to sit at the table to which the hostess led us.  I fully admit I was incredibly nervous and feeling a bit panicky.  He asked if I needed a Xanax and I asked if he had one.  No, he did not, I knew it was a joke.  He said he would suggest some alcohol, but it was a BYOB and he doesn’t drink, so no beverages had been brought.  That left me with time and a hopefully kind dinner companion to calm my nerves over the course of the date.  NSNG was very nice, said I looked like my pictures and he was happy about that.  They were all taken in the last three months, so definitely recent and hopefully indicative of my real appearance.  I really did feel better the longer we talked and felt pretty good about things by the end of the meal.  He suggested we order dessert as he had checked out the menu online and saw the icecream had a resemblance to dog crap.  I told him he wasn’t really selling that with his description but agreed to try it.  He seemed kind, funny, and genuine, maybe a bit dorky but I am too, so who am I to judge that?  We basically had to leave as the restaurant was closing, we had talked that long over our dinner.  He walked me to my car and hugged me.  He texted me an hour later and said he would like to see me again.  I agreed that I would like that too. 

NSNG messaged me the next day and suggested a game night a couple days later as he thought that might make me feel less nervous.  I had some apprehension around him coming to my house (we met at mine as he has a 15 year old son who was home at his place), as it felt a bit forward for a second date to me, but given that I had been so crazy nervous at dinner, I thought maybe being in my house, with my dogs, on my turf, would make me feel more comfortable.  So, I said ok. There was some back and forth over the next day or so on what games to play, he suggested Scrabble, which I frustratingly suck at.  I won spelling bees as a kid, am an avid reader, have a decent vocabulary, but truly suck at Scrabble.  I trusted we would figure it out when he got there.

The day he was coming over, I made sure my house was clean, I dressed nicely (nice jeans, sweater, black boots), and I was making chocolate chip cookies when he got there.  Baking is my thing, my stress reliever, and I figured I was killing a few birds with this stone – I had promised baked goods to a coworker later in the week, it makes my house smell good and welcoming, gives the impression that I am domestically inclined (at least as far as baking), and gives NSNG a parting gift either way.

He showed up right on time with a dozen roses.  I was surprised and pleased by this turn of events and thanked him for the flowers.  I finished the cookies with him hanging in the kitchen talking to me which did make me feel less nervous.  I was doing something I like, something familiar, and I didn’t feel like I was under observation.  Or if I was, it was an observation that I felt comfortable with and accepted.  Once I had them packaged up, including a container for him, I suggested a card game I like, and he agreed.

It wasn’t one he knew, so I went over the rules with him and let him have the first round as a practice round.  He picked it up fairly quickly, but I still kicked his ass at it.  Not unexpected as it was his first time playing.  I asked if he wanted to play again and he said no, let’s watch something on tv.  I suggested a comedy we had discussed at dinner that he had not seen but said he was interested in seeing.  Again, he agreed.  I put on the movie and we sat on the sofa.  He pulled my hand so I was sitting next to him, which was kind of unexpectedly nice. 

15-20 minutes into the movie, he started kissing me.  It has been eight loooonnnnngggg years, people, so yeah, I kissed him back and we ended up making out.  After a bit he started putting his hands under my clothes and I stopped him when he tried to put his hand down my pants.  I was interested, but absolutely not ready to sleep with him after my crazy long hiatus.  I hadn’t even shaved as I knew I didn’t plan to have sex that night.  We talked a little more and he left not long after that.  

Now I haven’t heard from NSNG (Not So Nice Guy) in days.  Asshole ghosted me because I wouldn’t fuck him on a second date.  I am disappointed in him for being such a cliche.  But even more than that, I am irritated with myself.  I used to be so much better at picking up on guys like him.  I was better at reading guys and not being snowed by their crap and thinking they are better people than they end up showing they are.  I really think part of me thought that I had gotten to a place in my life where I am older, more mature, and looking for more than just sex, and that guys my age would be at that same point – at least most of them.  I fully admit the wisdom with which I am crediting myself comes with a grain of salt, as I am oppositionally defiantly dating in part to prove to my son, and myself, that I am capable of a normal relationship, and I still feel like I have no idea what the fuck I am doing half of the time. 

So back to square one.  Or square 51 if we go by my age, or square 130 something if we go by my track record and continue numbering like a Word document. Do I completely stop trusting myself and my judgement?  Do I assume every guy is just looking for sex?  Do I start looking at the guys that I totally can’t see myself dating just to feel safe with guys I date?  Do I just give up and go back to my (self imposed) celibacy and solo life?  Do I invest in a new vibrator?  I almost feel like dating is an addiction I kicked eight years ago and this brief taste has left me wanting more.  I convinced myself I was ok alone, but I really am lonely.  No offense to my dogs, but even though they are super vocal, the conversation leaves a lot to be desired.  And I have to admit being thisclose to having sex again, holy shit, I miss sex.  I think I am going to add this chapter to my history, pick myself up, and try again.  I am online already, it isn’t that hard to pop into the app and see if anyone promising has messaged me.  Maybe this time will be different.  At the very least, I have ruled out everyone in my dating history*, so that has to narrow the pool at least somewhat, right?  

* The footnote to the history – yes, 007 has popped up repeatedly over the years – always with him contacting me first.  I have never initiated that mess back into my life on my own.  Every time ended the same, with him not being willing to date me or saying something so shitty, I lost interest in dating him.  The last time was about a year ago.  He was telling me about some youth coaching he is doing and said he felt like I didn’t have any interests.  I have tons of interests I have tried discussing with him over the years, from baseball, to reading, to baking, to my job (I once sent him an article about something I was working on and was particularly proud of being a part of this thing that will be life changing for many people. It was a five minute read, but when I asked him if he had read it, he claimed he didn’t have time.), to my interest in dating him.  It felt like the Grinch’s heart shrinking back down three sizes that day, with the realization that he just has no interest in me.  I probably have always known that, but it hit differently when he said that to me for some reason.  He has stayed away since then.  He isn’t blocked, which tells me the grinchy little heart still feels something for him, but I don’t know what it is.  I don’t think about him all the time anymore or feel like I did something wrong to not work out with him.  If he contacts me again, and I am still single in this dating saga, yeah, I will probably talk to him.  I would not let him sabotage an actual relationship though, so I do have some personal boundaries there.  Who knows?  Maybe I will still be single in 20 years, assuming I live that long, and hoping the pack of dogs I own then don’t eat my face when I die alone.