Meh

Okay, I did it.  I went back to online dating.  Four weeks, three apps and two dates later, I called it quits.  It was the same nonsense all over again.  There’s been no change in my experiences with – or opinion of – online dating.  It works for some people, but apparently I’m not one of them.  And I have neither the energy nor the desire to continue with it.  So I’ve kicked it to the curb again, and feel loads better as a result.

Here’s how it all went down this time.

I haven’t been on OkCupid for years.  Back in the day it was the source of most of my online dates.  Well, they’ve made changes and not for the better.  You can still message anyone, but they can’t see your message unless they “like” you back.  And the number of users has dropped precipitously.  Last time there was an endless supply of matches.  This time I exhausted all possibilities within a few days.  I collected 35 likes but only one was mutual.  Her profile didn’t give me much to work with, and this was our exchange:

Did we date once?  Did we talk once?  Was she trying to be funny?  We certainly didn’t fuck, I know that much.  But I never heard from her after that, so it will forever be a mystery.  Two more weeks went by without any new matches or messages. All I had to show for my efforts was that head-scratching conversation.

*delete account*

Next up was Tinder.  I never had much luck with it in the past and it was the same this time around.  Little activity, lack of conversation, flakiness, suspiciously fake-looking profiles… Meanwhile I had over 50 matches on Bumble and a slew of conversations going.  Goodbye, Tinder.  I burned through many of my Bumble matches, not hesitating to unmatch with those who failed to impress.  I was most popular with 28-35 year-olds and it didn’t take long to line up two back-to-back dates.

#47
She was 35 and a police officer.  Only a couple years older than myself but seemed more mature than that. Byproduct of her job, perhaps.  We met at a sports bar for dinner and drinks and quickly settled into nice, easy conversation punctuated by a number of laughs.  We seemed to be enjoying each other’s company.  Midway through she casually mentioned she was recently divorced.  This is the second or third time that’s happened on a date.

*theme from Jaws starts playing softly in the background*

Yeah, I’m starting to encounter this.  Well, she didn’t mention having kids, so I guess it wasn’t as big a deal.  Although, that’s something else I’ve been running into.  There’s a number of single moms out there who don’t disclose they’re single moms until they think it’s safe.  That happened several times during my latest stint on Bumble.  Sorry, but your personality is not going to overcome my dislike of kids.  Best to be upfront about it and not waste either of our time.

But I digress.  We stayed there for an hour and a half, and then I suggested going across the street for brews and board games.  It was a really cool spot and a popular hangout for people in our demographic.  She enthusiastically agreed, but in between getting up from the table and reaching the exit she changed her mind, saying it was late and she ought to be going.  I walked her to the parking lot and hugged her good night.  She texted me the next day and we went back and forth a little, but eventually things dropped off and that was that.

#48
This one was cute as hell – and she confided that she thought I was too – so I was pretty excited to meet her.  We met at a cheesecake place near my house and I liked what I saw.  She seemed a little more my speed, but the more we talked the more she appeared to be a homebody.  Nothing much in the way of hobbies or activities either.  Hmm.  I wasn’t sure what I could do with her, although certain extra-curricular activities came to mind as I eyed her up and down.  We called it a night after a couple of hours.  The next day I invited her to see a band play at a brewery but she politely declined, claiming other commitments.  Then she unmatched with me.

#49…?
I wouldn’t really count this as a date.  It was hardly even a meeting.  I was suspicious from the start, since her Bumble profile was nothing but pics of her performing and links to her music website and YouTube videos.  We talked music and she said I should come see her play at a bar that Saturday.  I did, but when I got there I saw that I wasn’t the only one she invited out.  I barely got to speak to her either.  My hunch appeared to be correct.  She was using Bumble to promote herself and her gigs.  Not the first time I’ve run into that either.  I’ve seen bartenders do the same.

I had two other hot prospects after that.  I really wanted to meet them both, but for reasons unknown they suddenly stopped talking to me.  One of them asked if I had an Instagram, which I thought was a little odd, then went quiet after I supplied my handle.  I didn’t post anything untoward on there, so I don’t know what happened.  The other unmatched with me after a few days of silence.

Eventually I ran out of Bumble matches, and I deleted the app a short while later.  So I got that out of my system.  I’m sure this is the point where my readers are going to suggest Match or Zoosk or Hinge or Coffee Meets Bagel or Duck Meets Goose or Nut Meets Bolt, or some other dating app.  Not interested.  I’m just going to do like my friend told me:  “Don’t date.  Just go out and meet people.”  Which is exactly what I’ve been doing, and it’s already bearing some fruit.  More on that in the next post…

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Itchy

I haven’t been on a date in months and I’m feeling the itch again. Not to mention it’s almost two years since I’ve gotten any action, so I’m getting antsy there as well. I chuckle when I read some bloggers griping about going a few days or a couple of weeks without sex. Oh?  Do tell.

Dating has been on the back burner this year. I’ve been focused on other things, and now I’m back at work so that’s consuming a lot of time. There were a few outings and social gatherings but I haven’t met anyone that way. I’ve yet to go back on Meetup, but I’ve also been considering giving online dating another go.

Yes, I know. I’ve sworn it off a million times and keep talking shit about it. But part of me wants to keep at it until I succeed. Others have, so why can’t I? If nothing else, it’s a good way to keep my skills sharp. When I met Rebecca (the old-fashioned way) I felt like I was applying everything I learned from all my online dates. So I guess it wouldn’t be a total waste of time.

If nothing else, it’ll give me stuff to blog about. But the thought of making a new profile, finding matches, wading through all the nonsense again… I don’t know if I can do it. We’ll see. If I do go that route, I think this time would be different. I feel like I’m a good place.

Stay tuned.

Interview

I’ve been interviewed by a fellow blogger, Unleashing the Cougar!  Follow the link to her blog and check it out:  Interview with the Formerly Unfortunate Virgin

Springtime

Spring at last!  While I enjoyed my three month vacation, it’s nice to be back at work and enjoying (slightly) warmer temperatures.  I’ve crossed a few minor items off my to-do list, made progress on a few others, and came up with a new goal:  visit every winery in the area.  Five down, 30 to go.  That in itself could be a blog, but I don’t really have much to say on subject.  I go there for the scenery more than anything.

I’ve received a flurry of activity and a bunch of new followers after my last post, Politics.  Welcome, all! Don’t expect many political posts from me, although I have toyed with the idea of a separate blog devoted to the issues.   Then again, I don’t feel like I have anything especially unique to add to the discussion.  Not to mention there are already those who are more knowledgeable and can put things way better than I can.

In other news, there’s absolutely nothing happening on the dating front.  Zip, zero, zilch.  No dating sites or apps for me because I’m still intent on meeting someone in the real world instead.  Except… I haven’t been making any effort on that front lately.  I’m too busy doing my own thing right now.  Eventually I’ll put myself out there again, but until then dating is on the back burner.  Don’t fret – there’ll be more disappointing dates to read about before long.

And finally, I’m being interviewed by a fellow blogger!  Unleashing the Cougar  submitted a list of questions and I’ve been working on my answers.  That’s nearly done, so look for that in the near future.

Politics

Never before have I seen so many dating profiles giving space to politics: “no Trump supporters,” “proud Republican,” “pro-choice feminist,” etc.  Screening potential matches this way may seem silly to some.  But with one’s politics comes a set of values.  What you believe speaks to the kind of person you are.  And with everything going on in America these days, I’ve been examining my own preferences and dealbreakers.

When it comes to dating I’ve never been especially picky.  Attractive, child-free, with the right personality and sense of humor… those were the main criteria.  I grew up very conservative and never thought I’d date a liberal, yet my high school girlfriend was just that.  Things were great as long as we avoided that third rail, but I wasn’t averse to dating on the opposite side of the aisle anymore.

My politics underwent a sea change over the next decade and I emerged on the left, eventually settling slightly left-of-center.  I think of myself as an independent though.  I chalk my evolution up to disillusionment as well as my open-mindedness.  I try to avoid confrontation and be a good listener.  I ask questions more than I argue, and probe others’ opinions rather than push my own.  However… when it comes to certain things, I simply can’t agree to disagree anymore.

Trump immediately comes to mind.  Never mind his policies – it’s the blatant hypocrisy and narrow-mindedness of his supporters that I find the most galling.  People on the right are making excuses for Trump that they would never make for a Democrat. Furthermore, facts don’t matter to a lot of them either. Why would I want to be with anyone like that?  Indeed I’ve unmatched several women on dating apps after discovering they were ardent Trumpers.

What’s more, he also gives voice and cover to some of the worst elements of society.  Of course, not all Trump supporters are racist and xenophobic bigots.  But racist and xenophobic bigots are Trump supporters – such as my dad.  He’s always been a strong conservative but he’s embraced Trump with a gusto I’ve rarely seen.  Of course he would – with his remarks about women and minorities, they’re like two peas in a pod.

Then there are feminists. Now, there are feminists like JBlondie (a blogger friend)  and others that I’m totally down with, who are capable of calm discussion and can actually take a joke.  Then there are feminists who go batshit if you use the wrong word or phrase.  I’m all for equal rights, but conversations shouldn’t feel like navigating a minefield.  Not for nothing, but if it’s a micro-aggression, shouldn’t it just make you micro-angry?

I remember one girl on OkCupid getting on my case for saying “gender-biased” or “gender-specific” things and flipping out when I used the term “friend zone.”  She also groused at me for not answering enough feminist-related match questions.  Then she wanted to do weird things like paint my fingernails.  Um, no thanks.  And before you ask, she was a real person.

Then there was another feminist, who was all into “Womyn’s Rights.”   We got on well enough, but when I was trying to plan our first date she shot down every suggestion I made.  When I asked her for a suggestion, she told me that I was the man so I had to come up with something.  I could have pointed out the irony of that, but chose to bow out instead.

Then I was friends with an uber-feminist.  In between Facebook posts of her hairy legs and armpits and “I hate men” memes, she wrote something to the effect that men should embrace feminism because it equals better sex.  I was privy to a related New York Times article (Does a More Equal Marriage Mean Less Sex?), so I linked to it thinking it was interesting food for thought and relevant to the discussion.

However I came back to find angry, essay-length comments from her.  Not only was she incredulous and outraged over everything in the article, but she accused me of taking time out to search for this article specifically to contradict her. Never mind the fact that I’d had it bookmarked on my computer for two years.  She also accused me of “furthering the oppression of women.”

Wow.  Nothing like confusing your friends for your enemies.  Needless to say we don’t talk much anymore.  Meanwhile I shared that article with JBlondie, and not only did she not get angry but said she could even relate to it.  That just drives home the point that when people are too far right or left they become rigid, unreasonable, and insufferable.

That’s really what I’m trying to avoid, and I’m certainly making more of an effort to do so nowadays.  But those are two groups of people I’m wary of. I’d rather not engage with Trump supporters, and I approach self-proclaimed feminists with trepidation.  Oh, and then there are vegans.  I don’t mind the passive ones – rather it’s the ones who won’t shut up about it.  Not to mention our lifestyles would clash horribly.

What are your dealbreakers and preferences when it comes to dating and politics?

Five

Just marked the five year anniversary of my blog.  Wow… I can’t believe it’s been that long.  I’ve come a long way since I started this, although in some ways I still feel like I’m in the same place.  While I’ve finally shaken the albatross of virginity, my sexual experience is still frustratingly limited.  Another year has ticked by with little to show for it.  However I did have a flurry of dates after my experience with Jane.  Unfortunately they were all a bust and I consigned Bumble to the rubbish heap once again.

#44
First one up was a 37yo nurse.  85-90 percent of the women I see online are teachers, nurses or social workers, so she fit right in.  And once again I seemed to hit it off with someone older.  Only four years older, but still.  She messaged me saying my pictures were awesome, that I seemed like a fun/funny guy, and that she’d love to chat.  So we chatted, and before long things were pretty flirty.

We met a few days later during her work break.  I’ll be happy never seeing the inside of a Starbucks ever again, but it was quick and convenient.  We were also keen to meet and didn’t want to put it off any longer.  I liked her and thought we got on well, despite her dropping a bomb about being married before.  I had no idea.  She had to get back to work at the end of the hour.  She gave me a quick hug, and when I asked about seeing her again she said “we’ll see” and trotted off.

I knew what that meant.  Sure enough, she went from texting 24/7 to complete radio silence.  Didn’t respond to my follow up either.  Apparently that date didn’t go as well as I’d thought.  But I had an old violin I’d wanted appraised and the violin shop happened to be right across the street, so it wasn’t a wasted trip.  They told me they could fix it for 300, or buy it from me for 100.  I went with Option B, and that’s another item off my longstanding to-do list.

#45
I double-booked for the second time in my life.  A few hours after I met Nurse Ghost, I went out to dinner with a 32yo who worked for a nature conservancy.  It was nice to talk to someone with a unique career, and in a field of great interest to me.  We also had much in common with our musical and artistic backgrounds.

She warned me that she was shy and awkward, but that she was also very forward and didn’t have a problem making the first move.  Shy and awkward, but forward?  Uh… okay.  However when we met she was neither shy nor awkward nor forward – just disinterested, evidenced by several glances at her phone. I’ll admit my own interest was dampened when she disclosed that she was a single mom.

Buzzkill.  I did my best to keep things light and fun, but I didn’t seem to be making any headway.  She asked little about myself in return, and by the time the check came it was clear neither of us was keen on prolonging the evening.  Afterwards we hugged good night went our separate ways.  By the time I got back to my car I’d already removed her from my contacts.  I’ve added and deleted more girls’ phone numbers than I can count at this point.

#46
I was almost ready to throw in the towel but I had one more lined up – a young hot 26yo.  I almost couldn’t believe she was interested in me.  She was a teacher (the number one profession of online daters).  We had a shared love of animals, the outdoors, being adventurous and trying new things.  We compared our to-do lists and decided to try an escape-room challenge together.

We settled on the “Killer Countdown.” She joked that she scared easily and might be clutching onto me.  Then she wanted to FaceTime to make sure I wasn’t a psycho before we got locked in a room together.  I’d never FaceTimed before.  It felt a bit weird but it was cool at the same time.   We chatted for ten or fifteen minutes and expressed our excitement about meeting.

The next night I met her outside the escape room place.  She came round the corner already looking less than enthused.  Turns out she reread the description online and learned we started the challenge chained to the wall, and she didn’t like that idea.  Before I could worry about that, we still had to figure out how to get into the building since the doors were locked.  I joked about that being part of the challenge, but she didn’t make a sound.

We ended up having to go around the back, and she was even more uncomfortable when she discovered we were the only ones there.  It’s common to be part of a group, but it was just the two of us.  You should have seen her face.  Well, I’d bought the tickets online and they were non-refundable.  There were five other rooms to choose from so I suggested we try a different one – maybe something less scary like the Game Room?

Nope, she didn’t even want to do that.  She grimaced at me and suggested we go somewhere and for a drink instead (which had been the plan for afterwards).  Sigh.  So I talked to the guy there and managed to switch our tickets to the next night, but I already sensed she wouldn’t be joining me.  As we walked out of the building she hinted that going for drinks would have been a better way way to get know each other than an escape room challenge.

I felt like a total ass when she said that.  Was this really a bad idea?  Then I was annoyed and bewildered, because I had included her in the decision-making.  This shouldn’t have been a surprise.  I didn’t spring this on her out of nowhere.  And what happened to all that jazz about being adventurous and trying new things?  What happened to the bubbly, energetic girl I had FaceTimed with?  She was walking along with a somber expression like we were going to a funeral.

I tried cracking another joke to lighten the atmosphere.  I’d stalked her Facebook and knew she was political, so I said, “meanwhile there’s a real life escape challenge going on in DC – they locked 100 Senators in a room and they have until midnight to prevent a government shutdown.”  Still nothing.  Tough crowd.  We made small talk and then we were accosted by a homeless person.  I didn’t understand any of his rambling speech except for his last sentence when he asked for some money.

I was in a charitable mood – plus she was watching me – so I fished out a dollar and gave it to him.  Then she gave him a 20-dollar bill.  “Wow, that was really generous of you,” I remarked as we continued down the sidewalk.  That finally animated her.  She launched into an impassioned speech about how she doesn’t judge people for their circumstances and it’s hard to ask people for money and why shouldn’t he have enough to get a meal, etc. etc.  Okay, I get it.  Just tell me I’m stingy then.

Before we met the homeless guy I was already wondering why I was bothering with this chick.  Apparently she was wondering the same about me, because she was texting every two minutes at the bar.  Each time I’d stop talking and wait for her to put the phone down.  I asked her about her teaching and her eyes lit up as she gushed about working with developmentally disabled kids.  Otherwise she was a bit clammed up.

Another text came in.  She picked up her phone yet again and I was stunned when she asked if I minded her friend Zachary joining us.  Apparently he lived in the area. Say what?  Were things going that badly that she needed the phone-a-friend lifeline?  I was so caught off guard that I didn’t know what to say besides, “um, no, I don’t mind.”  I figured she must have been really uninterested to pull a stunt like that.

In retrospect I should have just said good night, but I stupidly sat and continued talking to her.  I had a tall glass of beer I didn’t want to waste, and a small and silly part of my brain that thought I could still salvage things.  As soon as we finished our drinks she asked if we could cut things short so she could go meet her friend elsewhere.  Fine, whatever.  I waved her off, and erased her from my phone before she even reached the door.

Thus concluded one of the weirdest and worst dates I’d ever been on.  At least she bought her own drink and gave me the money for the escape room ticket, so I didn’t spend a single dollar on her ass.  I’ll give her credit for that much.

***

I was in a bit of a funk after three bad dates in a row, but a good night’s sleep cured all.  But upon reflection, many of my online dates went like that.  Either I thought they went well but apparently didn’t, or we got on well in text but there was a disconnect in person.  I’m sure most of those dates would have flopped regardless, but at the same time I can’t help think I should have had a little more luck out there.  Especially when I read about the online dates other bloggers are going on.

Of course, dating is harder as a guy.  I’ve also had more success offline than online, as I’ve noted before.  I’m still convinced that I’m better served getting off the apps and putting in the effort meeting people the old-fashioned way.  Half of what we communicate is through body language.  Chemistry is best figured out in person, without pretense or expectation.

So I’m shifting focus back onto the real world:  I went to another jam session, talked to some new people and may potentially join a new band.  I attended my old band’s fundraiser.  I’m getting back on the open mic circuit (I mean it this time).  I signed up for a Habitat for Humanity build.  I’m volunteering at my friend’s animal sanctuary next weekend.   I’m scouring Meetup for new activities.  Things are happening.

Kiwi

Fortunately my escape room tickets did not go to waste.  I had a do-over the following night with a friend visiting from New Zealand.  Second time was the charm for the Killer Countdown, and this time we were part of a group.  Of course.  And it wasn’t scary at all, nor did they lock the door or really chain us up (fire code regulations).  Not to mention we were on camera the whole time.  It was a hell of a lot of fun.

Afterwards Kiwi and I went to the same sports bar on the corner (returning to the scene of the crime).   It was trivia night and we got in on that after missing the first few questions.  (Too bad, because they were about musical instruments and I would have gotten them all right.)  Finally we went to a really cool place across the street for brews and board games.  I had a good time, but it was almost like being one of my online dates.  Kiwi said she had fun but seemed so flat and bland.

Was she always like that? Then again, this is the same chick I watched Planes Trains and Automobiles with and she didn’t find it funny at all.  A weak chuckle at most.  I’d asked her what she thought of it and she was like, “I thought it was annoying, but I understood the point it was trying to make.”  Jesus.  Between that and Bad Santa, I’m thinking I should compile a list of movies to watch with potential friends/girlfriends in order to vet them properly.

Our next outing proved that it wasn’t me – at least as far as Kiwi was concerned.  I met her and her mother and her friend (also from NZ) and we went into the city together.  If it weren’t for me talking or asking questions, there would have been near silence in the car.  We were munching on pretzels when someone pointed out St. Patrick’s Cathedral, and I was seized with inspiration.  I did a bit on Jesus and The Last Dessert that I thought would have killed, but I was greeted with more silence.

Of course, stand-up comedy isn’t my thing… I know because I’ve tried that as well.  I seem to be funnier when I’m not trying.  On the ride home I kept my mouth shut, but they still said hardly anything.  When Kiwi’s brother called from Alabama, their mom put him on speaker phone and it was nothing but one-word/one-sentence answers back and forth for ten minutes.  Christ.  Are all New Zealanders like this, or am I just too New York for them?

But it was a nice change of scenery for a day.  And while Kiwi was here we went ice skating, to One World Observatory, and to the Shake Shack (it was awesome).  My goal for the winter is to cross as many things off my to-do list as possible.  Items keep rolling over from previous years and it’s getting rather lengthy, but I’ve been making good progress lately.  Next up I’m going to try some new recipes and burger joints, explore some local history sites, and do some painting.

Instagram Girl

Even after she flaked on our date, she’d message me every once in a while and we’d chit chat.  Eventually she made noises about getting together so I took that opportunity to ask what happened.

Me:  “I know we were supposed to go on a date a couple of months ago but then you said you couldn’t make it… I didn’t think you’d be interested in meeting me after that.”

IG Girl:  “I’m sorry, I have issues hahah.  I really overthink a lot when it comes to the opposite sex.  Negativity consumes me.  I always choke up at the last minute.  What if he didn’t like me?  What if he finds me annoying?  What if I’m not cool as he thought I was?  That kind of stuff.  I’m working on that, though.  My confidence with myself is slowly getting better.”

Then she apologized because her hormones were all out of whack and she was feeling lonely.  Good grief.  So I still feel like a dodged a bullet.  If nothing else she sounds like work.  I’d rather be involved with someone with more confidence and less issues.  Otherwise… been there, done that, didn’t work.

I haven’t heard much from her since, nor have I reached out.  I’ve moved on.  And that’s the round up.  So there’s nobody else on my radar, no prospects in the pipeline, and I look to be sexless and single for the near future.

But, as I’ve found out, things can turn on a dime.

Downtown

So, my next post was supposed to be about politics and dating, and indeed I have several pages of rambling notes I’ve been agonizing over. I’ll get to that post eventually, but I have to write about something else first.

I met someone new.  Here’s how it happened:

It all begins with Winery Girl.  We still talk on occasion even though she’s had a boyfriend for the past two years.  Funnily enough, she actually took his virginity.  He had to wait six months to have sex with her though because – as she put it – she’s not a whore.  Uh… okay.  I wasn’t sure what to say to that.

She’s not too crazy about her boyfriend.  He’s basically a seat-filler because she can’t stand the thought of being single again.  She’s also been using the BFF function on Bumble to find new female friends.  She’s having a hard time of it, since all she sees are girls with nose rings and that’s a huge turn-off. I know that because she’s been griping to me and sending screenshots.

Winery Girl dared me to go back on Bumble to see how many nose ring girls I could find.  Ok, why the hell not?  I thought it might be funny.  And since I was treating the whole thing as a joke, I put in next to no effort.  I only posted one (albeit unique) picture and put one sentence in my profile.  Within a couple of hours I had nearly 40 matches from my careless swiping.  I hid my profile before things got crazier.

I spent the new few days culling the herd.   I decided that if I was going to entertain anyone on the app, then they’d better stand out.  A good portion expired without a message.  Many messaged with nothing more than “hi” or “hey” or “what’s up” so I deleted those.  Several messaged me and I responded, only to hear nothing further.  I deleted them as well.  The remainder matched me in goofiness and witty banter, and Jane was the finalist (no nose ring, btw).

#43
We got on so well that I asked her out, despite my original intention not to ask anyone out.  (Yeah yeah, I know…. so much for swearing off online dating.)  Our first date was a few days later at a wine and cheese place, and we were as fun and flirty in person as in text.  However she had a few more extra pounds than were evident in her photos.  Hmm… well, okay.  Not enough to be a deal breaker.

It was light and easy and comfortable with her.  I could relax and be myself.  Still missing that spark from meeting the old-fashioned way, but still better than most other online dates.  We spent a good chunk of our first date planning future dates, and we were at the place until closing.  I walked her back to her car, which happened to be a few spaces from mine.  We stood there talking until the well ran dry and then there was a slightly awkward silence.  “I don’t know what happens now,” Jane giggled nervously.

I did.  I wrapped her in my arms and kissed her. I didn’t hesitate or wonder if I could or should, I just went for it.  I wasn’t even nervous.  Big change from when I was going on dates three years ago.  She really got into it, too.  Almost immediately she was frenching me and running her fingers through my hair, and almost immediately I was super hard.

Our second date was that Saturday.  Jane needed help stringing Christmas lights on her tree so I gallantly offered my services.  She proclaimed that there would be no sex until at least Date 5 or 6.  No problem, I assured her.  However, I remembered Rebecca wanting to wait, yet we fucked on Date 2 when we couldn’t control ourselves any longer.  So with that in mind I came packing a box of condoms.  Just in case.

When I got to Jane’s place I couldn’t help notice the lavish furnishings.  She seemed a bit materialistic, which she confirmed by telling me how much she liked to shop.  She also told me she liked being spoiled.  Fortunately I’d brought a bottle of wine along, but I frowned to myself.   I wasn’t going to overthink things, but I couldn’t help imagine our lifestyles clashing down the road.  No matter.  I decided to not worry about the future and just enjoy the present.

I also couldn’t help but wonder whether Jane wanted kids…?  It never came up in conversation, and she was already 38.  In fact she was a year younger than Rebecca was.  Hmm.  39, 38… for some reason older women seem to be the only ones I’ve been having any real success with.  Interesting.  I do seem to connect better with those a few years older.  And I do find them appealing in a way.  That is, as long as they’re child-free.

We ate take-out and then I helped her put the lights on the tree.  Unfortunately, while the boxes were labeled the same, the two strings of lights didn’t match.  Dammit.  We sat on the couch gazing upon her half-and-half tree.  Then we snuggled together to watch the rest of The Santa Clause on TV.  That didn’t last long.  I’d been there for over an hour, and I was running out of self-control.

I reached over, cupped her chin in my hand, and tilted her face up to meet mine.  A heavy make-out session ensued.  God, it felt so good to do that again.  First time in a year and a half.  Before long I was sprawled on top of her.  After a while of grabbing at the hem she finally pulled my shirt over my head.  Yes!  This was happening!  Once it was off I asked whether she wanted to move things to the bedroom.  At the very least it would be more comfortable than the couch.

“We’re not having sex, but we can do other stuff,” she said.  I assumed “other stuff” meant oral.  Who’s the lucky boy? I thought to myself.  I’d never gotten a BJ to completion before, so it sounded like it might be a good night!  We resumed making out with some ferocity, and eventually my hands made their way to her chest.  I hesitated a bit, wondering whether she’d let me cup her breasts through her shirt.  She did.  Yes!  Her shirt came off shortly afterwards, followed by her bra.

I’ve fantasized about it many times, but actually removing a girl’s shirt and bra is truly a magical experience.  I don’t think it’ll ever lose its luster.  I relished the skin-to-skin contact, spending eons with my mouth on her neck and tits.  I started inching my way down, sucking and kissing and licking and nibbling as I went.  As I approached her belly button, I wondered how much further I could go.  No girl had ever let me go down on her before.

One time with Rebecca, I’d barely started on her when she pulled the blankets around her and proclaimed she was cold.  I guess that meant we were done?  After that, anytime my face ventured too far south she’d stop me and tell me she wanted me inside her.  Wasn’t going to argue with that.  Plus, I figured that like a lot of women she was self-conscious about how she looked or smelled or tasted down there, although she looked tantalizingly perfect.

After a period of time Rebecca told me she wanted me to go down on her, and I said I’d be happy to oblige.  I sent her descriptive texts about how I wanted to put my head between her legs.  Unfortunately that was also around the time she started getting weird and told me she was feeling overwhelmed and needed space.  Whether my texts contributed to that, I don’t know, but in any case I approached Jane’s nether regions with caution.

I hooked my fingers in the hem of her pants and pulled them down. Her panties came with them, and she assisted me in pushing them off.  Then I started to tease her.  I worked my mouth along her inner thighs, first one leg and then the other as her breathing intensified.  I kept teasing her until finally I was face-to-vagina.  My mouth hovered over her lips as I waited for the red light, but she didn’t seem like she was going to stop me.  She was naked and waiting.

So I took the plunge.  I went all-out, working my tongue in and out and all around.  I kept that up for a while, occasionally coming up for air and another mini-makeout session before going downtown again.  This time I stuck my tongue in even deeper, sucking on her clit while working my fingers inside her, trying to remember everything I’d ever seen or read.  Her moans and cries grew louder and louder and I smiled at her reactions.

Suddenly I felt a wave of heat as her body shuddered, and she wrapped her legs around my head and nearly yanked my hair out as she came.  Wow.  That was intense.  I made her cum two more times like that before I stopped.  I’d been at it for at least a half-hour and I needed a break.  My mouth was parched.  She held me tight to her chest and I enjoyed being suffocated by her 36Ds (I’d peeked at the label when I took her bra off).

“You’re bad,” she said.  “You’re not as innocent as you look.”

I gave her an evil grin.  “Definitely not,” I said.

“I didn’t think we were going to do all that…”

“I didn’t so either,” I said, laughing a little.

“What’s so funny?”

“Can I tell you a secret?” I asked, then immediately debated whether I should.  Ah, why the fuck not.  I wanted to see her reaction.

“Sure!”

“You’re actually the first person I’ve gone down on…”

There was a pause.  “What do you mean??”

I told her I meant just that.  She actually sat up and made me look her in the face as I said it again, because she wanted to make sure I wasn’t lying.  Then she goggled at me.

“But… like… how did you know how to do all that?” she sputtered, astonished.  “YouTube?”

“Google,” I grinned.  “Was it really that good?”

“Yeah,” she said, sinking back into the couch again.  “I’m still trying to catch my breath.”

“Well, I’m sure there’s room for improvement.”

“Well, you can practice as much as you want on me,” she said with a kiss.  And then I revealed a little more of my history to her, which further shocked her.  She couldn’t believe that not only was she the first I’d given head to, but only the second I’d been intimate with.  “So I’m your first vagina…” she said dreamily.

However, I was getting the sense that she wasn’t going to reciprocate, and I was right.  Dammit.  While disappointed, I didn’t whine or complain or make her do anything she didn’t want to.  Instead I was just glad I’d had my first opportunity to give oral and I did my best to make it count.  And I quite liked it.  I wanted to do it again.  And I would have gone down on her again had my tongue not felt like sandpaper at that point.

By then we were halfway through The Santa Clause 2 (a sequel which did NOT need to be made).  We cuddled on the couch for a while before moving to the bedroom, but only to sleep.  I’d already figured on staying the night, especially since it was snowing and the roads were treacherous.  She put on her PJs and I stripped to my boxers.  It didn’t take long before we were fooling around again.  We were spooning when she told me I could hold onto her breasts.  No problem!

Her shirt came off once more and I went to town, especially after she told me she likes her nipples pinched and sucked, which I was more than happy to do.  Then I sat against the headboard and told her to lean back against me.  That way I had a great view and easy access to her tits, and I fondled them to my heart’s content. Finally I ended up lying on top, grinding myself against her.  She bucked her hips against me in return, and went harder and faster until she came one last time.

Jane assumed I came too after I rolled off her, and was astonished to hear I hadn’t. Yeah… dry humping doesn’t do it for me.  And her hands never ventured past my waist, true to her word that she wasn’t going to touch me.  Which was a shame, because I had the biggest erection ever and would have loved to have shown it off.  But getting so worked up for so long was a mistake.  I went into the bathroom to whack off, but it was too late.  Wham.  Blue balls.  Jesus that shit is painful.

But I had to relieve myself or else I was going to be wired all night. After that I was able to sleep, and as I drifted off I mused how surreal it was.  If somebody had told me two weeks earlier that I’d be in a new girl’s bed, I’d have said that was crazy.  Yet there I was, and her bed was comfortable as shit.  I didn’t stay for breakfast as I had to get going, but we made plans to meet again during the week.

The following Tuesday we had a bonafide movie night.  And I take movie nights very seriously.  I actually watch the movie, and I even have my own popcorn machine.  She was surprised, but even more so at my choice of movie: Bad Santa.  Not only is that one of my annual holiday flicks, but I chose it specifically to test her sense of humor.  That is critical to me, and I was having doubts.

Well, she did not find it funny.  While I was roaring with laughter, she was going “awww!” every time the kid was onscreen.  When it was over I wiped tears from my eyes and relayed the tale of when I saw it in the theater with my mom and brother, and how people kept turning to stare at us wondering why we were laughing.  “Yeah, I was wondering the same thing,” she said.  Um, because it’s a comedy?  Yup, as I’d suspected we were definitely a mismatch.

After that we had a quiet time snuggling and chatting.  No fooling around, no groping, no making out… I wasn’t getting all worked up again for nothing.  If she wanted to wait to get physical, then we were going to wait.  Until then I was content with running my fingers through her hair, massaging her head and neck and shoulders… all the while marveling at how amazing it was simply to touch another human being.

Eventually we called it a night and I took her home.

We had a fourth date lined up – a Paint Nite – but there was more goddamn snow and it wrecked our plans.  She said she was feeling sick anyway, so that put the kibosh on the next few days too.  During that period I noticed our communication dropping off.  I was holding up my end but she was getting quieter.  Sigh.  My gut told me what was coming.  I’ve been down this road a million times.  So I waited.  Finally the word came down the pike:

“I’m sorry for the late response I have been running non-stop and can’t seem to catch up! I am an idiot for taking up a second job- I have to be at work at 6 am. This is just such a busy time of year etc.. plus holiday, plus my trip, I’m not sure if this is really a great time for me to start a relationship. It’s not fair to you. You are a really nice, sweet, kind of guy and you deserve a girl that has time to give you. And unfortunately I can’t be that girl. I realized all of this today as I finally have a chance to catch my breath and think…”

My suspicions were correct.  And it sounded like a polite way of saying, “I’m just not that into you after all.”  Which would have been fine, because I was starting to feel that way about her.  But I gave her a chance and it was fun while it lasted.  So I told her “no worries” and that I understood.  Thus concludes my latest dating experience.   So while 2017 won’t go out with a bang, at least I got to eat pussy for half an hour and play with tits for another hour.  It was a good thing I went down on her when I had the chance, because who knows when I’ll get another one.

I’m still convinced that Bad Santa was the beginning of the end for her.