Older Woman Date

—Tuesday, February 14, 2012—

I had long wondered how Valentine’s Day would play out during OHD, and while I hadn’t expected to be going out with someone 19 years my senior, it also didn’t seem like the craziest idea in the world, given what my world had become.IMG_1663

Lois was ahead of me getting to the restaurant, Crispo, but only by a few minutes. She texted me to let me know that she was at the bar. I texted back that I was running late but I’d be there in a couple minutes.

Walking in at exactly 6:30 p.m., I gave the host my name for our reservation and then greeted Lois. Technically, I was on time. She said hi, rather casually, and I said hello back. It was a little awkward. I’d have hugged her but she was seated in a chair facing away from me and she was not exactly exuberant. There were certain indicators that told me when a hug might be appropriate and I was not seeing them.

I apologized for making her wait and she reminded me that I was not late. I knew that, but I was being polite, I guess. I made some comment about how, “If you’re on time, you’re late.” She said that was silly and I realized that maybe self-deprecation wasn’t the way to go with this one. Most women delighted in letting me shit on myself.

Only a minute later, probably less, a host came by to grab us and asked if she had settled up at the bar. She said no and needed to flag down the barkeep. I thought about offering to pay, but it seemed silly. After all, she had ordered the drink while I wasn’t there and she was 45 years old. I figured she could handle it. Lois paid eventually, though it took a while to get the bartender’s attention. Once the bill was settled, we were seated by the host in an intimate alcove with a few other small tables. 

Allow me to explain how it came to be that I spent my Valentine’s Day on a date with a 45 year old woman. I found Lois on OkCupid while targeting older women specifically for this date. She not only responded to my initial message, but she was quite enthusiastic. She mentioned she even had gray hairs for that authentic older woman experience. I thought she was cute in her photos and her enthusiasm was unmatched (she was also the only one to respond, but let’s not allow that to sully the fact that she was a seemingly great choice for this date). 

Over the several weeks leading up to the date, we had texted quite a bit and, surprisingly, we had been exchanging pictures. However, Lois’s texts were not overly flirtatious. She didn’t use exclamation points or emoticons the way women 20 years her minor did, so it was hard to tell if she was flirting. Then one day, she sent a photo of herself. It wasn’t anything too revealing, but a photo of herself nevertheless. Then the words, “Your turn.”

This sort of exchange was something I had never participated in — back and forth picture sharing. She wanted to see me in my boring work clothes? Or what I looked like on a random Tuesday night? Okay, I thought, I’ll play your game.

This continued for a few weeks and at various intervals. The closest it came to being sexual was when she sent me a picture of her tummy in order to show me a scar. Like I said, these weren’t explicitly sexual exchanges. However, in explaining all of this to my friend Danielle the night before my date with Lois, she was 100% certain that Lois was looking to sleep with me.

So this was where we were at. This was the cougar’s den I had walked into.

Though it may seem like an odd choice, I had actually suggested going out on Valentine’s Day for a couple reasons. First of all, going out with a totally random stranger, as opposed to someone I knew from real life already, carried far fewer implications for romance. No one would assume anything if they heard we were going on a date. Secondly, the true potential for romance between me and a woman nearly 20 years my senior was so low that it didn’t seem likely that, even as strangers, we might accidentally stumble upon some kind of Valentine’s Day romance. I wanted to go on a risk-free date for Valentine’s Day and this was just about the safest option possible.

I knew ahead of time that Lois lived in the New Jersey suburbs and that she had two kids, so Danielle’s theory that she was trying to sleep with me seemed to have some hurdles to get over, but I was very interested to see where the night would lead regardless.

As I came to find out, Lois had been to Crispo a few times before but they were for work outings, she told me, not dates. That was a relief, because I would have felt like a stupid amateur if this was a common date spot for her. Especially since I had found it on Yelp! and I didn’t even know if it was any good. I hoped it was a decent choice and she said that it was.

I admitted to her that I had been flying blind while planning this date, so my fingers were crossed. She admitted that she’d actually sat in the exact same alcove previously. Well, I wasn’t going to win her over on my originality, but perhaps my youthful charm could make up for it. 

Lois told me that her day had been a little slow at times when I asked her about it, though it was usually pretty busy, she pointed out. I actually didn’t know what she did for work, so I asked about that as well. She worked in education and she’d been with the same organization for 20 years. She loved it, she told me, before asking me about my day. “It was fine,” I reported back, “Nothing unusual.” Take note, people: This is how you kill it on a date! Be as uninteresting as possible.

We discussed dinner options and what looked good from the menu. I ordered a glass of Montepulciano, as I am wont to do, and Lois continued with her white wine selection from the bar. We decided to split an asparagus and prosciutto appetizer and though it had some cheese on it — which I found suspect — I figured I could survive. This brought up the topic of being picky about certain foods and we talked about that briefly. For entrees, Lois ordered some ravioli dish and I went for the orechette with sausage and broccoli rabe.

Switching gears from foods I found disgusting, Lois asked which desserts I liked. “Chocolate. Anything chocolate,” I told her. “Like, chocolate lava cake?” she asked. Yes, chocolate lava cake was amazing, I agreed. Lois made some crack about the molten center of the lava cake and it confused me. I believe she said, “So, you like the warm, fudgey middle?”

She said this in a very suggestive tone which made me think that she was flirting with me. I nearly laughed because it was delightfully silly and the only thing that she could have been alluding to was anal sex. And I was fairly certain that wasn’t what she was going for. 

Her next question was even more flirtatious…I think. “Is there anything better than a fudge middle? Maybe a cream center?” Lois asked. Since I didn’t know quite how to react, I responded literally, saying “No, I don’t like cream centers. I much prefer chocolate ones.” I felt kind of bad for taking it literally, but it really wasn’t the style of flirtation that I excelled at and I felt uncomfortable referring to desserts as a proxies for sex things.

I mean, the creamy center was like…lady cum, right? Which sure, I guess I was into, but it was an awkward allusion to make within the first 15 minutes of a meal. Would I rather have creamy vaginal sex or fudgey anal sex? I doubt it was that specific in her mind, and I’m sure that Lois was just flirting and had perhaps arbitrarily picked those dessert items to use as her proxies.

However innocently unintentional it was, I immediately processed those symbols into very real sex things. Most likely, it was just my 26 year old mind at work, assuming the worst, and she was merely being playful.

Some flirtation wires had definitely been crossed, but we managed to get through it all right.

The asparagus appetizer was good. In fact, I was a big fan of it, even with the cheese, so that was a good sign for the meal to come. The food would at least be fairly decent.

I asked Lois about her kids, and I was able to remember their ages from our text messages, which was a solid detail to recall. I also made mention that I had been to her town a couple of times, since I had a friend who lived nearby. It probably wasn’t super common for her to go out with a 26 year old Massachusetts native who was familiar with her suburban New Jersey town, so I hoped that scored me a few points as well.

By the time our entrees arrived, there was one thing that I had noticed most above all, which was that Lois made tons of eye contact with me. I think she might have been trying to eye fuck me. That, or she was simply asserting her maturity and confidence. Either way, I was not capable of reciprocating on the same level and it made me feel like a juvenile. To be clear, Lois didn’t make me feel like a juvenile — I made myself feel like a juvenile because I couldn’t sustain eye contact like a goddamn adult.

“So I’m your older woman date?” Lois asked as we ate. She sure was, I confirmed. “Am I the oldest woman you’ve ever dated?” she followed up. She sure was, and by a lot.

I think the next oldest person I had ever dated was maybe 33. Lois told me that she usually dated mildly younger men, somewhere in the world of 35. It almost sounded to me like she kind of got off on that shit, being the older woman. That’s not meant to be a slight though — I could totally see the appeal of it. It must have been fun for younger guys to chase her or for her to see if she could ensnare any of them. She seemed to take pride in the fact that she was my oldest date, which was really cool. The last thing I wanted was to be on a date with someone who was embarrassed to be out with me.

Lois asked a lot of questions and I appreciated that she did much of the first date heavy lifting. “Do you get tired of dating?” she asked me, which was a question I had answered many times before. I told her that it wasn’t something I tired of, and since she’d been dating quite a bit herself, I asked her if she ever grew weary. She said she didn’t because she simply enjoyed the fun of it all.

She could appreciate a date for what it was: a fun way to meet a new person. We had very similar minds when it came to this point and, aside from all the pleasant conversation we’d been having that night, this was the first thing that we really connected over. I was definitely more into the date once we started down the path of talking about dating. 

I asked Lois what her favorite part was about dating. Mainly, it was simply that each date was new and exciting. Plus, guessing whether or not you’d get a kiss was fun, she said. I definitely agreed with that — I had garnered a bit of a reputation as a kissing bandit by this time in the project.

With that point of agreement, and considering Lois’s earlier flirtations, I started to feel like we’d kiss before the night was out. 

We also talked for a while about honesty in dating and we were on the same page with that as well. Ambiguity was enemy number one and we both agreed that people should just lay out their intentions if they knew them, especially if the other person was in the dark. There was a moment where I felt like Lois was going to simply tell me that she would have sex with me, which was kind of a crazy thing to anticipate, but it seemed like we were on the precipice of some kind of similar moment. She didn’t say that, of course, but the build up left me thinking I might be in for some kind of frank reveal from her.

The food was excellent and at one point during our meal, Lois commented on a couple seated behind me, in the corner, who were making out in a fairly flamboyant fashion. Her reverence of them seemed to suggest that she wouldn’t mind doing the same.

By the time dinner wrapped up, we were having a good time together and I offered to pay since it was Valentine’s Day, and if there was any day set aside for chivalrous bullshit, it was this one. She refused my offer, which made sense, and informed me that we were going to split the bill and that was how it was going to work. She was assertive and I was into her straightforward rejection of chivalry.

As we exited Crispo, I asked Lois if she wanted to drop in somewhere else and grab a drink. She was very interested and suggested a couple places since she knew the area well. The first bar we attempted was packed, so we tried another. We walked by her work on the way and I could see her office from the street. It was some fancy shit. I was impressed.

We found a low key tavern and grabbed two seats right at the bar, ordering a couple classes of wine shortly thereafter. Lois stuck with whatever white wine she had been drinking previously and I went with a glass of Pinot Noir.

Chatting over our chalices, we made pleasant conversation that was both fun and mildly flirtatious. She informed me that I looked just like my pictures, which didn’t always happen. I said the same was true of her. Then again, I had never met someone from the internet who was totally misrepresented. It sounded like she had. We both agreed that it was stupid and incredibly odd to put up pictures of yourself on your dating profile that didn’t look like you. There was no success to be had in that strategy.

I thought about asking her if her tummy really looked like the picture she had sent me, but I didn’t have the balls to ask such a weird, and almost creepy, question. I just thought it would have been funny.

Even though it was fairly early, I could feel myself getting tired already and I sensed that Lois was in the same boat. I mentioned this to her and she corroborated my feeling. I used the bathroom and paid the tab, to which Lois did not protest. We thanked the bartender and exited to the street.

Lois asked where I needed to go to catch a train, and to be honest, I didn’t really know where I was going yet. Ariana and I had been texting earlier that day and I had told her that if my date ended early enough and if I still had the energy, we could grab a drink. It was nothing scandalous, since she had a serious boyfriend, but he had a hockey game and she was left with nothing to do for a few hours.

Plus, there were no West Village trains that could bring me to Astoria, so they were all equally useless to me. I told Lois that I would walk her to a train, and then figure out my next move, since we were going different directions no matter what.

I followed her to the train and once we had walked down the stairs to where we needed to part ways, we paused for a minute.

Well, this was fun. Yeah. It was. Thanks so much for everything.

None of the forwardness that Danielle had predicted was present. Lois’s suggestive comments earlier in the night had not resulted in an invitation to her place or anything like that. It looked like it would end like just about any other date.

As I leaned forward to hug her though, it was clear Lois wanted to kiss. She had dropped enough hints and there was also no good reason not to kiss her.

We made out for a minute or so, there on the subway landing, but it didn’t get too steamy. Though she seemed to have confidence in spades when it came to flirtation and conversation, she lacked the physical assertiveness I fantasized about from an older woman. She made it clear that she wanted to kiss, but I was the one who had to take the initiative. I wanted a cougar who grabbed me by the nuts and pulled me close, not someone who hung back and left me to my own indecisiveness.

After parting ways with Lois, I met up with Ariana at a bar near Union Square for a drink. I wanted to spend Valentine’s Day with someone I loved, if only for an hour, and Ariana fit the bill perfectly. She gave me a valentine and some chocolate. It would have been a great end to my Valentine’s Day, except that it wasn’t actually the end of my night.

Ariana jumped into a cab just before midnight to meet up with her boyfriend, but as we’d prepared to leave the bar, I had received a few text messages from Cecilia, looking to meet up.

Figuring that I might as well make my Valentine’s Day as eventful as possible, I caught up with Cecilia at 36th Street and Park Avenue. We went home together to consummate the most romantic of holidays the only way we really knew how.