Adventures in Babysitting–Er, Dating

The Queen of Cougars, Demi Moore, and Ashton Kutcher

As I said before, I was hesitant to go on a date with The Kid, the 28-year-old guy who happens to live rather close to me. Although it seemed we had quite a bit in common, I was afraid he and I wouldn’t be at similar stages in our lives.

I remember 28. I thought I knew who I was, but I really had only scratched the surface of growing into that person. And I’ve dated so many men in their mid- to late-30s these days who still have no clue how to navigate an adult, long-term relationship.

Still, I decided to go for it.

I found out the Kid was taking college courses as a freshman in high school. He has been working professionally since he was 16. He dropped out so that he could get his GED and move on more quickly in his chosen path, and doors kept opening up to him. He easily makes more than double what I make, he’s brilliant and incredibly driven, but he’s such a laidback guy…the opposite of intimidating. We share many similar passions and interests, including music, technology, nutrition and health.

Our conversations are like Double Dutch jump rope—weaving in and out at different spots, requiring attention and thought, while also being playful and fun. He sincerely wants to know what I think about a particular topic, and he listens to what I’m saying, asking follow up questions or looking into books or documentaries I bring up.

We’ve gone out twice now, and he’s on his way to Texas for a 10-day vacation. I don’t feel the crazy zing of knock-you-off-your-feet romance with him. But that seems besides the point. Whether it’s a low simmer to boil relationship or we continue to build a friendship, I’m really happy that the Kid and I are getting a chance to get to know each other. He’s good people. And I think it’s hilarious when he says to me, “You ready to go, kid?

Rocking the Cradle Part II

After things went so well with The Kid, I stepped into my date with BBoy, only a few years younger than I, with less hesitancy. We had chosen to go on a hike for our first date. Considering that most of my recent long walks ended up with me on the floor, this was a rather bold and risky move, particularly on one of the hottest days of the year to date. However, I figured I was up for the challenge.

After the excruciating hike—both of us were covered with sweat, I was relieved to see—we wound up by the waterside, where we sat and talked for hours. We covered all those taboo first date topics—past relationships, religion, politics, money. BBoy is a great storyteller, and he had me laughing much of our time together.

The hours flew by, so much so that when we finally decided it was time to leave, we were astonished to discover it was after 8 p.m., more than four hours after we first set out. The sky deceptively gave no indication we had moved beyond the evening.

One concern? He hasn’t been in a relationship in five years. He claimed it was because he’s choosy. His last two relationships, and really only significant ones, ended in fidelity. He said openly that he’s looking for a wife at this stage in his life. I almost fainted hearing that come out of his mouth; it’s unusual to hear this sincerely from guys of a certain generation these days.

Another concern is the heavy sarcasm. I can handle a rather large dose of it, but if that’s the only way you’re relating to people, it gets old after a while, even when it’s not pointed condescendingly at you. Also, we disagreed on one of the taboo topics, but again, that’s not something new, though ideally I’d like someone more open-minded than BBoy on that front.

I actually found BBoy a little more immature than The Kid, but that had nothing to do with age and all to do with attitude. No shocker there.

Sometimes It Really Is Too Good To Be True

So, one day the following week I receive the OkCupid alert that HE is checking me out.  He happens to be a very attractive musician who lives the next town over, so I shoot him an email. Before too long, this guy, let’s call him The Player, replies, “Yours is certainly the most interesting and intriguing emails I have ever received on a dating site before!” He recently moved here from out West, loves to hike, writes and plays his own music and suggested we get together to do all these things.

The Player and I somehow became Facebook friends (I know, I know!) I saw pictures of his adorable daughters—one of them an adopted girl from Asia with special needs; another thing to connect on as I had worked in special education for a couple years. I saw that he had a gazillion “friends,” many of them probably fans of his music. And then I read one of his Notes.

You know those passive-aggressive notes—addressed to someone in particular but because it’s under the heading of ‘Note,’ and written with enough ambiguity, every “friend” can read it and try to guess what it’s all about.

I knew he was divorced, but this note made mention of another recent divorce after a brief marriage. When I asked him about this, he said he’d been married for 15 years to one woman, and then was married for one year, saying that had been really poor judgment.

He invites me to a show his band is playing in a couple days. In our exchanges he teases about how men must be chasing after me. I tell him he must have the same problem with the ladies. He replied that once they find out he’s a Christian, that sends most of them running.

Looking at some of his photos and comments he shares with his friends, I get a feeling…call it a case of déjà vu from the Christian Rocker. I ask him if he’s a Sunday Only Christian or an Every-Day-of-the-Week Christian.

Born Again "Bad Boy" Stephen Baldwin

Those of you with any experience with self-proclaimed religious folk, especially born-again Christians, know what I’m talking about. There are people who are go to church on Sunday, but throw out all the lessons learned all the rest of the days of the week and totally live it up until the next Sunday when they are back for the next sermon. And then there are Christians who live and breathe their faith every moment of every day.

Most Christians I have met who are around my age have been of the former persuasion. Especially in my generation, there are people who shout about their faith from the mountaintops but are bigger hypocrites, more judgmental, more promiscuous, party harder, etc than the average non-religious person.

I jokingly asked The Player which persuasion he was. He honestly said he was a Sunday-only Christian, trying to get back to an every day one. This wasn’t really a big deal to me either way, but since he said being religious affected his dating life, I really wanted to see if he would be straight with me.

Anyway, he asked me to see his band play that weekend. I took a day to get back to him because I found out we were watching my niece and nephew while my brother and his wife were out of state. So Saturday evening, the Player writes back saying, “I hadn’t heard from you, but I wanted to let you know I am meeting up with someone before the show. I didn’t want it to be awkward for you if you were planning on coming.”

After days of this guy teasing me how I must have zillions of guys chasing after me, I had to roll my eyes. A true player.

Supposedly, he and that woman instantly fell for each other, spent the rest of the weekend together. This past weekend, she and her kids spent the weekend with him and his daughters, “pretending they were the Brady Bunch,” he told me in a text. He had the nerve to ask me if it bothered me to hear about this. I said absolutely not; I was glad he found someone he was happy with.

Frankly, I was incredibly relieved to have escaped without being the next stop on his fickle women world tour.

Being Willing to Take The Leap

The Sunday before last, I was supposed to go on the second date with The Kid. We were going to go for a hike and grab lunch in one of my favorite areas in Massachusetts. I wasn’t overly excited for another day of punishing my limbs in a hike, but I was looking forward to the view and another day of great company and conversation. Yet before we could there, something, or rather someone, got in the way.

The Scot is someone who emailed me many weeks earlier. He lived in Long Island, yet I had popped up in his matches. He said he lost that email, but remembered my nickname, so kept searching the site until he found me. Anyway, it was a sweet email. We exchanged a few, IMed a bit, and then he disappeared.

Well, that week, the Scot reappeared. He apologized for going MIA, asking if I wanted to know why. I said sure, was it that he had met someone else? He said no, no, totally wrong line of thought. Apparently, he was thinking so far ahead, according to him, that he was imagining us liking each other so much that we’d wind up in some tortured long-distance relationship.

I teased, “Maybe we should try a phone call before we worry about all that.”

Love is Taking That Leap

So we did. Five or six hours later, we had established that yes, we had a really nice connection that was worth taking to the next step. In fact, we were going to go crazy and meet sort of halfway the next day. He would take the ferry to Connecticut, and I would take the train down to the town where his ferry let him off

It was spontaneous, reeked of the wildly romantic side of me I’d pretended was no longer a part of me (and he’s 40) and yet it sounded like great fun. I took a raincheck with The Kid, and made my way to meet the Scot.

We had a full day of getting lost in a part of the state I had never really spent time in. We found a tasty Indian restaurant, then made our way to a park by the Sound, where there was a hopping cover band playing and the beach was lined with sunbathers. We grabbed some ice cream and found a spot on the boardwalk to do more chatting, then moved our way under the trees.

The Scot was as sweet and kind, while also being funny and having a little wild side. He was up for adventures, is close to his family and has a strong group of friends. He is a great listener and I felt like we really enjoyed hearing what the other had to say. It was truly disappointing that the day had to end; we really had enjoyed ourselves, and yet the geographic distance between us was still acutely there.

Was it worth it? Totally. Sometimes you just have to take the leap, no matter how unrealistic the chances are. I got a text from him the other day as he was on his way to D.C. for work saying he should’ve asked me to come along. Next time, maybe.

There’s no rush. I had a lovely second date with The Kid before he went to Texas for 10 days. I’m totally caught up in this new, year-long program I’m studying online now, and I love the people I’ve been meeting through it and the things we’re studying. I’m focused on a new direction in my own wellness plan. There are still many other areas of my life needing care and attention.

So no, there’s no rush at all. Right now, I’m just enjoying the adventures that come my way.


6 thoughts on “Adventures in Babysitting–Er, Dating

  1. Ah… exactly the reason I enjoyed online dating – talk about variety. I’m glad the Player was a very short lived character and the outings with The Kid sound exciting. There’s something about being with a man younger than you that reminds us 30 someting women that there is hope. In fact, I’d go so far to say that there have been more youngsters I’ve encountered who had their lives together with visions and goals than those my age or older.

    As for this last one you mentioned and the distance? Don’t over think it. Just enjoy the moment.

    • Variety is the spice of…dating? It’s nice to have a good selection of men to choose from, though of the three I might pursue something with, they all work in IT. Ha. Still they have very different personalities, which is nice.

      I am with you about The Kid. We’ll see if we wind up just being good friends or if it turns into something. I agree, seeing younger people who have their act together is a really cool development. All this time that I’ve been looking to older guys, perhaps I should have been paying more attention to guys my age or younger. Plus, oftentimes they come with less baggage!

    • Thanks so much, Miss Melisa Mae. 🙂 I think having so many other things going on in my life right now, I have become detached enough from dating that I can see it with perspective. It’s meaningful to me, but it won’t make or break me if I have a man by my side right now…though it would definitely be nice.

      Definitely dodged a bullet with The Player.

  2. At 35, I tend to leave the door open 10 years on either side. I tend to date older women, and it’s rare that a 25 year old woman will interest me, but like you, I have seen how age and expected maturity aren’t always a match.

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