a great second date with Kyle

Are we having a moment? My second date with Kyle

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“Ann, are you telling me you and I both have dark blue cars with tan interiors?”

We hold each other’s gaze from across the table.

“Kyle, are we having a moment?”

Ann, indeed I think we are. Give me a second to recover. Wow.”

We burst out laughing.


Exactly when promised, Kyle picked me up in his car. Aware of his eyes on me, I carefully went down my stairs and tried to casually yet sexily cross my street. Guys, try it in three inch heels carrying a purse and a coat, on a street with potholes; it’s not the easiest.

I slid into his car, said hello, and he kissed me on the corner of my mouth. I resisted the urge to kiss him again. He accelerated just like I would down my street. We started to talk about each others day and the entire time I wondered if he was going to tell me where we were going.

About 5 minutes into the drive he said “Oh, so I didn’t know what your preferences were for dinner, so I picked something middle of the road. I hope that’s fine; I just made an executive decision. We’re going there now.”

“That’s great Kyle, no problem at all. I’m quite happy to not make decisions.”

I realized how that might sound so quickly followed up with “I mean, I like to make decisions, but I’m okay with not being the one to always make decisions.”

He laughed and said “Ann, I knew what you meant.”

I liked how he drove. Just like me: careful but aggressive. The conversation flowed through the drive, parking, and throughout dinner, and I can’t remember all the topics we covered. Family history, drink preferences (we share a love of a good Dark n’ Stormy), our children, travel, cars, and sports. The car exchange was one of my favorites – we had good banter.

The moment I sat down at the dinner table the top of my high waisted Spanx rolled down. Fuck. I knew it couldn’t be seen but it was highly uncomfortable.

We had some particularly fun conversational moments. At another point, when I started telling him about my family history and a few customs, he got a funny look on his face, so I asked him what he was thinking and he said he was wondering whether we’d do said custom on an upcoming date. It’s those little moments that make me happy on a date…because it means he’s forward looking.

That night I learned a lot of things I like about Kyle.

He has not spoken one bad word about his ex wife. In an earlier conversation, he demonstrated a similar philosophy as mine: the breakdown of a marriage is rarely about just one person. We each have a role to play, and when you have a child together you will always be connected. It’s better to have an amicable relationship.

Even more notably for me, the way he described his last girlfriend (they lived together and dated for over a year) was even nicer. They weren’t ultimately compatible but he simply said “she needed someone who was also going to have a 9-5 job and be there with her at home every single night.”

While he’s busy with work travel, his stories indicate to me he will integrate a girlfriend into his life. If he’s travelling somewhere during the week, he’ll ask her if she wants to join him for the weekend. Even if his friends and colleagues are around. That kind of thing. It’s similar to how I see things – busy doesn’t mean you can’t find time for someone important.

He has close friends and he does thoughtful things for them. He is good to his Mom and his brothers.

He skipped watching a big sporting event with his favorite team for our dinner. I even offered to go to a sports bar after our meal and he declined. His friends had been texting him like crazy during the dinner and he joked surely they should be okay on their own for a few hours.

He’s friendly to wait staff.

Concerned I was irritated at his last-minute cancellation earlier in the week, he proactively brought it up saying he knew he may have looked like a complete asshole and he was glad I agreed to see him again. I explained I would have done the same thing if the tables were turned, but I was a little worried when I didn’t hear from him the day before. He said “I know I’m so sorry I was rushing around and had to re-jig all of my travel for the rest of the week…” and I cut him off and told him everything was fine.

He likes to dance although says he’s not very good.

He went through a “less discriminating” phase (my term) after his split from his ex-wife (they’ve been apart for many years) but now prefers to date one person at a time. He said practically he simply doesn’t have time for it with his business travel, and doesn’t know how some of his friends successfully maintain a stable.

Like me, he seems to believe in internal locus of control and personal growth. I am starting to think these are the two of the most important beliefs for me in a partner. I don’t ask people what their opinion is on these (it’s the rare person who will say they don’t believe they control what happens to them), but the way people talk and the describe events in their life give me insight into how they think.

For those of you who were concerned with Tony’s daily marijuana usage and Ian’s over-drinking on our third date, you’ll be pleased to know Kyle isn’t a big drinker. He drank one cocktail at dinner.

We shared a dessert, he paid for dinner, and we got back in his car. We stopped outside my house at 10:30pm. I asked him whether he’d be interested in coming upstairs for a drink. He declined, saying he was pretty tired, at which point I remembered he’d traveled to and from a different city that day. He’d been up since 6am.

We proceeded to talk in his car for almost another hour. I had taken off my seatbelt and angled my body toward him. It was a calculated move also to fix my fucking Spanx which had rolled down again. I was afraid if he touched any part of my middle he would feel them and that would be awkward.

He said he’d love to see me again if I was interested.

Fuck yeah.

We were both away for the weekend and I explained I had my son next week, but perhaps if he was comfortable with it, he could come over for a drink one night next week. “Otherwise,” I said – and he finished my sentence for me, “I won’t see you until the week after.”

“Yes Ann, that sounds great. Tuesday it is for sure… Actually, let me know when you are home from your trip on Sunday. I may decide to come home on Sunday so – and we’ll do Tuesday for sure either way – but maybe I could see you Sunday night as well.”

My heart skipped a beat, if such a thing is possible.

I started to become hyper aware of being in his car for an hour, he didn’t want to come up, and I should really get going. But he’d made no move to kiss me. Should I just say “okay bye then” and leave?

I said “well okay, I know you’re tired, and we can talk forever it seems.”

“Yeah” he said.

I looked at him.

He looked at me.

Our faces were pretty close. Neither of us moved. My mind was racing wondering if he was going to kiss me.

I quietly blurted out “are you going to kiss me?”

He instantly said “yes” as he leaned forward.

It was exquisite. Then he apologized for not doing it sooner. I joked about it being an hour in the car.

We kissed again. He put his hand in my hair at the base of my neck. It was a wonderful, perfect, first kiss slow pace. We talked some more, and kissed again, first gently, then something shifted and he pulled me into him a fraction more, the kiss became a touch more insistent, and I felt his desire (no I don’t mean anything euphemistic about that, I didn’t feel any part of his body other than his arm).

That moment has been on high rotation in my head ever since.

I said “oh, wow… okay, I think I should go now.”

I thanked him again for a wonderful evening, he replied in kind, I got out of his car, walked to my front door, and waved to him as I went inside.

51 thoughts on “Are we having a moment? My second date with Kyle

  1. Ok this is going to be silly.
    Look up Rago shape wear, it’s extremely restrictive but it beats Spanx any day! It’s the good stuff. It NEVER rolls down
    Second: if your date leads to sex, how do u avoid a guy seeing your Spanx? I’m seriously dying to know this… Really.

    P.s. He sounds great!

    • I don’t like restrictive but I will look it up!!
      And it’s a good question, I would basically go to the bathroom at an opportune time and take them off… But that’s why I don’t like them. Too complicated lol…

    • Me too actually. Unfortunately I’ve found its a very rare man who will have sex on the first or second date and still respect you. Often they put you in a “not girlfriend worthy” box. They are out there but it’s not common.

      • I guess I’ve been lucky? Or maybe it’s because he can’t bring himself to think of me as a girlfriend? Not that I don’t count for him, but… yes, I know, I need to write about it πŸ˜‰

        • I’d say I’ve been lucky too, I have men like Ariel, Andrew, Jason, and Tony to count in that camp. But they aren’t typical in that regard.
          With your dancer? It does seem he’s not in a place to commit to you that way, but I don’t think it’s because of this reason particularly.

          • I agree, I don’t think it’s certainly not because I agreed to sleep with him on the first date. πŸ™‚
            And whatever his reasons… they’re his πŸ™‚
            As for my experience, I’ve mostly met men who don’t mind too much. Granted, some didn’t see me as GF material, but to know whether it was for that particular reason or for a different one, it’s difficult to know too. I’m trying to count right now, because I think my percentage of ‘sleeping doesn’t influence GF possibility’ is much higher than yours. If I don’t count those for whom it was clear from the beginning that there is no GF position available (my first FWB and Mike). I think I’m somewhere close to 50%. Granted, my experience in the area of dating is far from yours πŸ™‚

      • It is very rare. And it seems like they aren’t even aware that they do it. It’s like this weird process – if a sexual connection is made before an emotional one, it overrides everything and you are always thought of sexually before all else. I used to think that engaging with someone sexually, quickly, created intimacy. But the two are very different. I also used to mistake men’s sexual addiction to me as some sort of validation of my worth. If only I had known better lol.
        I also agree with you and Kyle when it comes to believing in the locus of control. However, I’ve also seen “evidence” that we’re also guided in our choices and thought patterns. We have to follow our gut and remain confident that we ultimately decide what we want and what we’re willing to do or not do, to get it. But that’s where our control ends — and sometimes the biggest gifts happen from things that are completely out of our control πŸ™‚ Keep enjoying the ride <3

  2. About the Spanks…so you go (at an opportune time) to the girls room and remove them. How long before the indentions in your skin disappear? If I felt a line where spanks used to be, I would assume that she was insecure. YOU ARE NOT INSECURE!! Be yourself in ALL ways! If the few pounds a Spanks hides makes a difference to him….you know what I’m thinking!

  3. He sounds wonderful so far!! Fingers crossed it continues! I really like that he didn’t put down his exes – a sign of a good man!

  4. All right—I don’t like this guy.
    He’s doing all my moves, but, making them succeed, the bastard. πŸ˜‰

  5. Ann, I have to say that after all the guys you have written about (Tony included), this one is making the best first impression on me. He’s friggin’ normal, no red flags, respectful, no drama. I’m so happy for you. Plus he apparently wants a real relationship, so he’s holding off on the sexual intimacy to make sure you are “girlfriend” material. That shows maturity, real interest in you as a person. Good luck!

    • Now if he’d just text me a little more…. I find it very disconcerting even when I’m sure it’s just him being busy and not a big texter. I sense he feels since we have dates and times locked down there is no need to communicate again, which makes me a little bananas.
      Especially because he’s made such a good first impression with me as well!!

    • I know!! It’s pretty awesome when they go well, but then it’s hard to keep the celebration in check and we never know what will happen next, do we? I’m becoming such a fucking cynic.

  6. I’m late to the party. I like Kyle, so far. I like that he played it cool and declined your invitation to come up for a drink after dinner. He wasn’t too tired to sit and talk, so he’s going to make it special and not be too easy. That takes will power and shows class. I am wondering where the chink in the armor is, as he sounds good. Hopefully no chink.

What do you think?