I was so keyed up Saturday night that it took me forever to fall asleep.  Sunday afternoon I sent The Singer a text saying, “I had an especially nice time last night.  How was choir practice this morning?”  Then I put my phone down and went merrily about my business.  However as the minutes turned to hours I started feeling anxious.  Something is wrong…I thought.  I felt it in my gut.  She often took a while to respond to messages, but I thought I could expect quicker responses after what seemed a fantastic second date.

Still, I bit my tongue and didn’t send any more texts.  I waited.  And waited.

Finally the response came this morning:


My worst fears were confirmed.  And I was stunned.  Seriously?  After several minutes I blinked away my confusion and replied:  “Wow… okay.  Totally not what I expected to hear. Obviously we came away with different impressions after the other night.  I don’t know what to say except good luck to you too then.”

I just don’t get it.  She seemed really into me.  Especially when we kissed.  Did I really misread things that badly?   I’ve been replaying the second date in my head, trying to remember if I possibly did something to turn her off.  Nothing comes to mind.  Except… maybe it was the kiss that did her in?  I’ve only ever heard good reviews  from the few girls I’ve kissed.  Maybe they didn’t want to hurt my feelings, but I know one of them certainly would have told me if I was bad at it.  Or maybe I wasn’t bad at it, but my kissing simply didn’t set off any fireworks for The Singer?

I ran my theory past one of my female friends, and she asked me if I used tongue?  I thought tongue was a bit much for a first kiss.  Perhaps if we had made out longer than a couple of minutes we would have graduated to tongue.  She insisted that I should have, otherwise kissing without tongue is without passion and tantamount to a friendly peck.  I’ve never heard that you should use tongue on a first kiss.  Now I’ve been surveying my other female friends to get their opinions.  So far I’ve gotten:

“Depends on the situation but typically yes”
“No, and if it turns into a full blown makeout session, only very little tongue”
“Let the woman lead a bit on that.  See how her body language is”

Interesting.  It’s something I’ve never considered before, but I’d be curious to hear your opinions.  Could something like that make or break a second date?  What other reasons would a girl not want to go on a third date?


While  I was waiting to hear back from The Singer, I went on another first date Sunday night.  Another OKC find.  We exchanged a couple of messages, had a half-hour phone conversation, and we set a date.  She thought we had a lot in common and I thought so too.  However, after our date I realized we didn’t have much in common apart from starting in the same career and a shared desire to remain child-free.  The first hour went well.  She went for a second round of drinks (I paid for the first and she paid for the second) and her body language was encouraging.  We were sitting facing each other on our bar stools, legs practically touching, but by the second hour I noticed there was more distance between us.  She had pulled back.  The conversational well was also running dry, so after two and a half hours I suggested calling it a night.  She seemed ready to go.

We hugged outside on the sidewalk, told each other “nice meeting you!” and said good night.  Then we went our separate ways.  I said nothing about getting together again. While I had something in mind for a possible second date, neither one of us really seemed to be feeling things and I don’t know what else we could talk about.  She had really bad breath besides.  Oof.

Finally, I had planned to see The Comedian again, but if you remember I was decidedly lukewarm about her after the first date.  I was going to give her a second look, but our texting fell off by mid-week and then she cancelled for Sunday afternoon.  Just as well.  I’m not going to pursue it any further.

First dates:  35
Second dates:  4
Third dates:  2
Cancellations:  9
Stood up:  2
First kisses: 3


It’s been ages since I’ve had a second date, but I went on one tonight with The Singer and I dare say it went pretty well.  The original plan was to go to the carnival, but the shitty weather put the kibosh on that.  We ended up going bowling instead.  There was an hour-long wait for a lane so we went into the bar area and had a couple of beers in the meantime.

We found a relatively quiet corner and had a nice conversation.  I found out that not only does she like Harry Potter, but she’s a Star Wars and Titanic buff too.  Score!  She’s very easy to talk to, and the huge mug of beer I had helped as well.  We also delved a little deeper this time, broaching the subjects of religion and politics and the cosmos.  We were pretty much on the same wavelength there too.  She took a lively interest in what I was saying and I was eager to learn more about her in return.

They finally called our names and we went out and bowled a couple of games.  She picked up the tab for those since I bought beers this time and dinner last time.  I appreciated the gesture.  After a couple of good frames I did a spin and a moonwalk, much to her amusement.  When we were done bowling we sat there chit-chatting for a bit before calling it a night.  She had choir practice in the morning and it was getting late.  I also didn’t want to overdo things.

I walked her to her car.  At this point my heart was throwing itself against my ribs.  We’d been texting all week and things got a little flirty the day before.  I was determined to kiss her before we parted ways.  I think she might have wanted me to kiss her after our first date, and I wasn’t going to make the mistake of not doing so this time.  Second date – shit or get off the pot.

We stood by her car making idle chit chat and it was clear she was lingering, so it was now or never.  I said good night and we hugged.  We pulled back a bit, and then I lowered my arms to around her waist and pulled her back in.  She realized I was going in for the kiss and she closed her eyes and tilted her face to meet mine.

As soon as I saw her do that I mentally shouted YES! YES! YES!  Then we connected.  It felt great.  Totally natural and not awkward in the slightest.  I let my hands roam around a bit, running them up and down her back, along her sides, and then reaching up and grabbing the back of her neck.  She pulled me closer against her, and when I put my hand on her neck she grabbed the back of my head and pulled me even closer.  We made out like that for at least a couple of minutes before finally coming up for air.  She opened her eyes slowly and let out a little giggle as she looked me, and then she put her head on my shoulder and just held onto me for a bit.

I said good night again and told her what a nice time I had, and she told me I’m a lot of fun to be with.  Then I said I’d be in touch very soon, gave her one last peck and floated over to my car.  I drove home in a happy little daze.  And now the big question is how to proceed from here.  I’m quickly approaching uncharted territory.  I have to figure out my next move and not screw this up.  I seem to be doing pretty well so far, though.  I’ve been cool and chill and patient, and I haven’t done or said anything weird or stupid.

Oh yeah – and I think she likes me.


First dates:  34
Second dates:  4
Third dates:  2
Cancellations:  9
Stood up:  2
First kisses: 3


I feel like I’m finally starting to find my footing here.  I have two second dates lined up for this weekend, one with The Comedian and one with The Singer.  It appears I’m finally about to smash through the first date wall. What’s more, a third girl gave me her number on OKC.  I called her up the other day and we had an actual phone conversation.

Normally I hate talking on the phone, but this time I felt perfectly relaxed and comfortable.  I was further surprised when I discovered we had talked for over half an hour.  I’ll take that as a good sign.  As it turned out, we both had previous careers in real estate.  That alone gave us plenty to talk about, but there’s a lot more ground left to cover.  Long story short I asked her out and we’re meeting up Sunday night.  This weekend is shaping up to be a busy one.

I’m really trying not to overthink things or get my hopes up.  I’m doing my best to continue with life in the meantime and not stress over whether things will go well or “omg will one of these girls finally be the one??”  After forty first dates I’m learning to be a little more chill and patient.

In the meantime I reconnected with an old friend.  An old female friend.  We haven’t seen each other in over three years and we met up for lunch the other day.  Like me, she’s a veteran of the online  dating scene.  We compared war stories and regaled each other with tales of our exes.  At one point she asked me, “so when did you lose your virginity?” and I was brought up short.

“Ah…” I began.  “I’ll let you know when it happens,” I said.

“Come on, seriously… when was it?” she asked as I laughed.

“I just told you, it hasn’t happened yet.”

“You’re being a total shithead!  Come on, you just said you were in a relationship for a year and a half.”

“Yeah, and in all that time she was afraid to go all the way with me…”

“You’re lying!  Look at me,” she demanded.  I looked at her.  “You’re totally lying! I can tell by your face.  I’m really good at reading people and the corner of your mouth is going up on one side which means you’re lying -”

“No, my mouth is twitching because I find your reaction most amusing.”

She sat back and stared at me.  “I still think you’re being a shithead.”

“Nope,” I said, and proceeding to describe how skittish my ex was and how long it took to make out or fool around with her.  She looked entirely unconvinced.

“So you’re a 31 year old virgin,” she said.

“Yup.  But I’m not worried about it.  I’ll find someone, it’s just a matter of time.  I’m slowly getting better at this dating thing.”

“How do you act?  Do you act like this when you’re on dates?” she inquired.

“Act like what?”

“Act the way you are with me right now.  Are you doing something weird when you’re on dates?”

I racked my brain.  “No.  Not that I can think of, anyway.”

She frowned at me.  “You aren’t telling them you’re a virgin, are you?”

I snorted.  “Of course not.  Why would I tell them that?”

I was flattered that she didn’t believe me.  And finally she told me I should get a prostitute, or do anything to get laid and just get it out of the way.  But I’m confident I’ll pull this off before long and do so on my own merits.  Just you wait and see.


…from an Italian restaurant.  I rarely do dinner on a first date, but I did tonight with The Singer.  She was the second of the three girls that canceled last Tuesday, so I shall adjust my counter once again since we successfully rescheduled.  The Singer is my second Tinder date.

We got there at the same time and she was even cuter than her pictures.  I liked her from the start.  I gave her a hug and we went inside.  We got a table in the back, and since it was Sunday night it was fairly quiet and empty.  Perfect.  I felt a bit more relaxed, comfortable, and in charge of my words than I was on the last few dates I went on.

This actually happened to be the same place where I’d gone on my first date ever.  But at that time we were just high schoolers getting pizza and soda.  This time it was a sit-down dinner, and the place had been completely remodeled so it was almost like being there for the first time.  And I dare say this date went much better than that one.  If you remember that post, you’ll know what I mean.

Anyway, The Singer is a music teacher, an operatic singer, and a choral director.  We had plenty to talk about with our combined musical backgrounds.  And then I found out we share a mutual love of waterfowl.  Major bonus points.  I know what we’re doing on our second date.  If there is a second date.  While things seemed to go pretty well, I feel like I already know how this is going to end, which is the way it always seems to end:  I’ll get in touch with her in a day or two about a second date and I’ll get the usual “Well, I had a fun time and you’re a really nice guy, but…”

Sigh.  But we’ll see.  I could be wrong.  I’ll know soon enough.

In the meantime I’ve been keeping in touch with The Comedian.  I don’t feel any particular attraction to her and I’m not sure what else to talk about either.  So I don’t think this is going anywhere.  However I have a new prospect who just gave me her number on OKC, so I’ll contact her tomorrow and see what happens.

First dates:  34
Second dates:  3
Third dates:  2
Cancellations:  9
Stood up:  2
First kisses: 2


California Girl doesn’t want to see me again.  I waited three days before texting her again:

Me:  Hey, how’s your week going?
CG:  Hey, week is going well.  How’s yours?
Me:  Things are awesome.  Work is starting to pick up.  I’ve also been thinking about our next outdoor adventure…

…since she had she’d be up for another one.  I let that hang for a bit but I didn’t get a response, so I followed up.

Me:  Weather looks questionable this weekend – would you settle for a food adventure in the meantime?
CG:  I’m not available this weekend, have friends coming into town from CA.  While I think you are a very nice person and enjoyed meeting you, I don’t think we are a fit and don’t want to waste your time.  Best of luck on Cupid!
Me:  Oh.  Not even as friends? I thought that was all you’re looking for right now? I thought we got on pretty well…what makes you say that?

At this point I figured I had nothing to lose by asking, so I did:

Me: And as far as OKC goes I’ve been on 40 first dates and little more. If you have any feedback I’d love to hear it.
CG:  Yeah, a lot of people go on many dates before finding the right fit. I think dating is just difficult in our day and age.
Me:  Well I’m sorry I won’t see you again.  Best of luck to you as well.
CG:  I don’t think my opinion represents all of your experiences.  If you want to know why I think you and I are not a fit, I’m happy to share my thoughts.
Me:  Yeah, go for it.
CG:  I think you are looking for more.  And I don’t feel we have much in common.
Me:  Maybe not but we hardly know each other.  I barely scratched the surface with you and there’s much more I wanted to know.  But I appreciate your feedback.
CG:  You asked me for feedback and I’m letting you know my experience.  I genuinely wish you the best.

However our texts crossed each other because as soon as I received that from her I’d already sent:

Me:  Just curious what made you think I’m looking for more?  Did I give off that impression.
CG:  You gave me a hug when before we left, you kissed me on the cheek when we met, and just asked me why you are struggling to get a second date.  All of those things to me indicate more interest.  And I feel this conversation is no longer helpful so I’m going to end it now.

Yeah, so that was pretty much it.  I should have just left it alone, but since I’ll never see her again I didn’t see the harm in asking.

Moving on…

Fortunately I already had another date lined up with The Comedian.  She’s one of the three Tuesday girls that canceled on me (so I’ll revise my counter).  She lives very close by and we met at the local ale house.  This time I made sure to dress up more than usual, especially since this was a less casual date than the others.  I waited inside the front doors but it turned out she was already inside.  When we saw each other there was a mutual hug.  No handshake, no kiss on the cheek, and no awkwardness.

We opted for a booth and thankfully the place was quieter than I expected.  Judging from the parking lot I thought it would be bonkers inside, but it wasn’t and we were able to have a conversation.  TC was even more inquisitive than CG, which I took as a good sign.  And when she’s not busy with school, she’s busy with her theater group –  singing and dancing and doing comedy skits.  Sounds like a good fit for me.  Nonetheless I made sure to hold back and keep my jokes PG.

When it comes to women I often feel like I have to walk a tightrope, waiting to be cast into the abyss for the slightest misstep. I second-guess everything leaving my mouth now.  It’s one thing to talk and act a certain way with your friends, it’s another to be that way with someone you’re meeting for the first time and I try to be mindful of that.  Especially when I seem to put my foot in my mouth more often than not.

In any case, things seemed to go pretty well.  We were there for two hours.  We talked about music, comedy, our respective upbringings and career paths…  I did my best to keep my rambling in check.  I feel I avoided any serious blunders.  I slipped in the occasional bright remark and she thought I was hilarious.  Then I even dared to share a few of my dating stories – a subject I usually try to avoid altogether.  Out of all the girls I’ve met so far, she has the clearest picture of my dating history.  Whether that’s a good or bad thing remains to be seen.  But she told me some of her own stories so we’re even in that department.

At the end of the night I suggested we get together again.  She said she’d like to as well. Yeah, we’ll see.  But she said she liked me and felt comfortable with me.  We gave each other a hug before we parted ways and I promised to be in touch soon.  I probably could have and should have gone for a kiss, but honestly I’m not sure how attracted I am to her yet.  I will definitely go on a second date with her if she accepts, and then I’ll get a better idea.

First dates:  33
Second dates:  3
Third dates:  2
Cancellations:  9
Stood up:  2
First kisses: 2