A Horse Wins a Race, A Guy Wins My Heart

I am 35 years old and I have only been someone’s girlfriend twice in my life.

The first time was in 1998. I was a senior in high school and dating Dave, an absolute sweetheart. I lost my virginity to him the summer before we went away to college. We stayed together until Spring Break of freshman year when the distance between our universities just made things too hard.

The second time was in 2005. I remember the moment when we addressed it. Max and I were driving to a professional basketball game after dating for a couple of months. Because I loathe uncertainty, I had to ask, “If someone asked me if I had a boyfriend, I should say ‘yes,’ right?” I chose to ask this while driving over the George Washington Bridge, just to ensure all of my anxiety levels were as high as possible. He looked at me like I had just asked him his name. “I sure hope you would say ‘yes!’” he answered. And that was that. 

If I ever want these, please smack me.

(Three years later, he asked me to marry him, and four years after that I would ask him to divorce me.)

A decade since that moment in the car with my ex-husband (and three years since my marriage died), Rick expressed that he wanted me to be his girlfriend. Whoah.

Unlike with Jason, when I wanted no part of being his girlfriend or any else’s, I actually like Rick too. We have been spending as much time together as we can since we met in the end of April and it’s been great.

When Rick brought up the G-word, I got skittish because that’s what I do. Yes, I’ve been hoping to find a relationship again for awhile now, but I’m one of those people who is perpetually single.

I really like being single. I’m good at it. I know what to expect. I know how to take care of me.

But I also know how wonderful it can be to be in a healthy, balanced relationship. Sure, it’s been long time since I had one of those, but I do remember the early days with Dave and with Max – the cuddling, the handholding, the first birthday spent together, the first road trip. And of course, the joy of sex with someone you really care about.

I told Rick I wasn’t quite ready for the labels yet, but I was getting there. 

I wasn’t seeing anyone else and I found myself thinking about him an awful lot. I felt excited about the possibility of… something… with him. Fortunately, Rick has been wonderfully patient with me every step of the way. He told me that he understood and that he wasn’t going anywhere.

Things changed a couple of days later at Belmont Stakes, the famous horse races.

American Pharaoh Wins the Triple Crown, Rick Wins My Heart

Rick had invited me to join him for the big event. He and his friends are into the racing and betting. Me, on the other hand, well I was tagging along for an excuse to day drink. Oh, and to meet his friends, of course!

I knew absolutely nothing about Belmont or horseracing, which made the day even more exciting for me. We rode two different trains to get out to Belmont Park on Long Island, just outside New York City. When we arrived, I was just in awe.

The facility was huge but still charming, with all kinds of seating both indoors and out. (We were in the Backyard, AKA the cheap seats.) Something about the park felt like a throwback, as if I were in a Disney movie like Mary Poppins. The people watching was incredible! The outfits were Vineyard Vines meets Kentucky Derby. To put it in perspective, there were men wearing seersucker suits and women wearing those huge hats like Kate Middleton wears. The crowd consisted of everything from the super wealthy to the hard up gambling addicts. The energy was palpable as we got closer to American Pharaoh’s shot at winning the Triple Crown.

Given that Rick actually understood what was going on, you would think it would be sort of annoying to be at such a big race with someone as clueless as me. But nope! He proudly introduced me to his two best friends from growing up. As we wandered the grounds, he explained the races and the betting (which was totally intimidating and confusing, hence my gambling all of about $25) so that I might appreciate the madness. And the entire time, Rick held my hand.

I had never seen or done anything like the Belmont Stakes, and I was experiencing it with a kind, loving man who thinks the world of me. How lucky was I?

It was a hell of a day! Even I understood that American Pharaoh’s win was a big deal.  

(Confession: I didn’t get out of my chair to watch that race because I was busy eating a soft pretzel with mustard. I didn’t want all that perfectly good rock salt falling on the ground. My love affair with carbs wins again.)

Much later that night, tired from alcohol and snacks and sun, Rick and I strolled from Penn Station to Grand Central. Hand in hand, I found us talking about my terribly conflicted feelings about motherhood. I won’t share the details of that very personal conversation, but I knew in that moment that things had changed for me. Rick wasn’t just another guy I was dating. This man actually meant something to me. 

It was a big day for a horse, and a big day for this divorcee. 

The next morning, while we laid in bed chatting about nothing in particular with our arms wrapped around each other, Rick paused.

“You are my girlfriend, right?” he asked.

There was only one thing for me to say.

“Yes.”

When was the last time that you realized you were in a new relationship?

The Art Of Dating Someone Who Is Not "My Type"

Well, this is an interesting twist of events.

I like a guy. Like for real. Like we hold hands and have sleepovers and we have made each other dinner. He calls me “baby” and it doesn’t make me throw up in my mouth. And guess who is not freaking out? THIS GIRL!

Because I actually like this guy – and he digs me, too! – I have been really hesitant to write about him here. In my blog world, someone ends up a punchline (e.g., the guy who dumped me because I’m allergic to dogs, the guy I dumped because he baked me brownies and then he gave me flowers).

But it’s exciting to finally feel this way, some 18 months after I decided I was ready to look for a relationship, so, I have to dish to you, dear readers.

You're not my type! Go away!
Wait, come back! I changed my mind.

As you might remember, I had put dating on the backburner, but I kept Tinder and Hinge on my phone because why not? Swiping left and right can be amusing while you’re waiting for your burrito or whatever. So, one night in late April, I ended up chatting with Rick on Tinder. 

Rick does not meet all four of the criteria for dating me:

• Age – My criteria has been maybe a year or two younger or up to 10 years older. He’s 37, so that’s perfect. (And, how weird is this… we have the same birthday!)
• College educated – Sort of. He didn’t finish undergrad. But, since he’s an electrician, he has a ton of related education and certifications. 
• Salary – Hard to say, but he definitely has more expenses than I do, which leads me to . . .
• No roommates – Well, she’s not a roommate. She’s his nine-year-old daughter. Yup, he's a single dad.

No, he wasn’t my usual type, but given that I’ve been single for as long as I have, perhaps my type is worth reevaluating. Rick asked me to continue our conversation over a drink. I said yes.

As I walked into the bar to meet Mr. Tinder, the usual online dating thoughts ran through my head: “Please be cute. Please be smart. Please be normal.”

My dating prayers were answered.

Relief #1 – he looked just like his photos (and he’s actually tall, for real!).  Good, because obviously I thought that he looked cute!

Relief #2 – it was just… easy.

We had a nice mix of small talk and real talk. But the best thing for me was my immediate sense of his warmth. He felt kind and open in a way that you don’t often encounter, especially from a man on a first date.

At the end of our date, he walked me to my car and asked to see me again before I left for my trip to Germany. I agreed. Again, he was not my usual type, but this was fun and so relaxed. He hugged me goodbye, and I got in my car with a big stupid smile on my face. What a gentleman! 

Three days later we met for dinner. Three hours later, he walked me to my car and kissed me in the street. It was a great kiss – that make-me-melt combination of sweet and sexy. I knew I might be getting myself in trouble, and in a good way.

Rick was definitely making me rethink the rules I have been trying to stick to for two years.

Outdoor country concert = best date ever.

Since I returned from my vacation, we have spent as much time together as our schedules (particularly his) allow. Each time that we have hung out, whether it’s date (dinner! bowling! Jason Aldean concert!) or just hanging out at home, we get closer and closer. It’s really cool. I have to admit that despite how very different our lives are (I'm at happy hour while he is coaching his daughter's lacrosse team), we have many similarities in how we view life. We have been able to talk about past relationships (we are both divorced) and our hopes for the future.

Rick is much better at articulating how he feels about me; I’m still guarded. But oh how refreshing to be with a man who is secure enough with himself, his masculinity, and his feelings to be so open! (Ahem, Ryan, take note!) And those other more closed off men were the guys who were "my type" -- at least superficially.

We are both crushing hard. It’s really scary… I have a million questions [fears], particularly because I have never dated someone with a child before. But I'm doing my best to be very present and just go with the flow. 

Next step -- meeting each other's friends. Keep your fingers crossed for me!

By the way, since I’m finally dating someone where I see relationship potential, of course, this means that yesterday Zach contacted me out of the blue to ask me if I wanted to fuck (he never wastes words). Then tonight Jason, the Incredible Sex – who I have not seen in nine months! – texted me to see if I wanted to have a “platonic drink.” I told them both that I’m seeing someone, so no. Much as I love me a good booty call, I would never risk a potential boyfriend for a frivolous fuck or allegedly platonic drink.

Have you dated someone who wasn't your usual type? How did it go?