Love at the Racetrack: Going Home Happy, Win or Lose

Pop Culture
A day at Saratoga can be perfect for friends, a family day out, or for a date. (Penelope P. Miller/America's Best Racing)

Stephanie was a senior and I was a sophomore. I worried, perhaps a bit too much, that our age difference was going to be an issue for her. I worried it was maybe something that would be embarassing for her. She was on the drill team. She was blonde. She was rich. This wasn’t the kind of girl I was used to dating. I mean, I was a sophomore, let’s be honest … I wasn’t used to dating at all.

Ordinarily, a girl like Stephanie wouldn’t really even talk to a guy like me at our school. But we had been on a school trip in Washington, D.C. and somehow while we were there we all managed to shed the stereotypes and prejudices that each of us accumulated in the halls of our high school. The pecking orders, the cliques and associations, it all seemed to go out the window. People who would never ordinarily associate with one another back home were now staying up late into the night spilling our life stories to each other, debating philosophy and politics, hanging out, sometimes even making out. Somehow, on that trip I felt like I was popular, and she and I seemed to click more than anyone else. We were an unusual pairing, for sure. She was popular and dated football players, driving them in her convertible to Wendy’s during lunch. I stayed in the cafeteria and did magic tricks for people. She went to parties. I went to punk-rock shows. But it didn’t matter because on the plane ride home she gave me her phone number and told me to call her and we’d hang out. It was, dear readers, on.

When I finally worked up the nerve to call her and ask her out, she asked me what I wanted to do. I offered that we should go to the racetrack and bet on horses. She said that sounded like an “awesome idea” and she laughed out loud. “You’re interesting,” she said. I felt like I was on the outside of my life looking in, like I was watching a movie about some other nerd in some other high school who pulled off an out-of-his-league coup. But it was actually happening to me.

Racetrack can be a great first date. (Penelope P. Miller/America's Best Racing)

She picked me up in her convertible because, if you remember, I’m only 15. We went to the track and I bought some seats in the grandstand. This, for me, was splurging. I usually walked to the track and I never sat in paid seats. I sat on the concrete steps outside with the rest of the bums. But I was trying to play a different part.

We pored over the day’s entries and I showed her a few things I knew about handicapping. She seemed at ease and comfortable. At one point, she held my hand. We circled the horses we each liked and planned out our bets. As post time for the race approached, I pulled out a wad of money and handed it to her to go bet. She looked flummoxed. Then a smile washed across her face.

“That’s right! You’re not old enough to bet!” She laughed and took my money and headed off to the window. We didn’t cash any tickets that day. She didn’t hold my hand. The next time I called her, I heard her tell her sister to say she wasn’t there. 


Rachel was a co-worker at a new job when I had just turned 21. Her last job before she came to work there was as a blackjack dealer at a casino. When our boss found out that I liked to gamble, he wanted to fix us up.

Rachel lived with her boyfriend, but our boss told me he knew it wasn’t going so great between them. He’d drop hints to each of us about the other one and say he thought we should go out. We both laughed him off and asked him to chill. I don’t know about her but I secretly hoped he wouldn’t.

Sharing a program at the track. (Penelope P. Miller/America's Best Racing)

Rachel was blonde with tattoos, including one that wrapped around her waist and would peek out in the space between her shirt and her jeans. It was a fairly involved piece and it drove me crazy imagining what it was. She was loud and funny and aggressive. Sometimes, she could even be downright mean. I liked that about her most of all. It felt like a privilege to be on her good side — like you had to earn her friendship, she didn’t just give it out free and for nothing.

After a number of months of working there, I heard through the grapevine that she and her live-in boyfriend had broken up, but that they were still living together, which was weird but was a normal thing in an expensive urban area. One day at work while chatting her up, I let it drop that I was headed to the casino that Friday night to play poker. She asked me if she could come along. Once again, folks, it was on.

When I picked her up that night she was wearing a red cashmere sweater with a plunging v-neck and some serious red lipstick to match. This was date attire, to be sure. When we arrived at the casino, I asked her if she wanted to get something to eat first and she agreed.

We went to the restaurant, which was fancy enough but still had TVs on the tables where you could watch the horse races and place bets while you ate. We chatted about horse racing, a game she knew well having spent so much time around gamblers. In addition to her time as a blackjack dealer, she came from a family of gamblers and knew her way around most things associated with wagering and chance. She told me her own stories of trips to the races, both horses and dogs, with her family and she shared some tips with me for how she liked to handicap winners. I couldn’t believe it. Was this the perfect woman? I grabbed a program and we looked over a race. I picked a longshot and made a stupidly large bet on it with the server, trying to show off. The longshot blew the doors off the field. The bet paid about $400. I suggested that we order lobster. I was head over heels. I convinced myself that this was the person for me.

But we never went on another date. She got back together with her boyfriend, who had never moved out. I never stood much of a chance. The tattoo, however, was a mermaid.


Katie and I started dating in secret, because we didn’t want any of our co-workers to find out. We were working on the road, staying at a hotel in Albany, N.Y., which made it even harder to sneak around, since our co-workers could keep pretty close tabs on our comings and goings.

Saratoga charm.

I proposed that we go spend a weekend away from the hotel together to avoid their prying eyes. It was August, after all, and Saratoga had been calling my name. She agreed, though she had never been to the racetrack before. I’m lucky her first experience was Saratoga. The whole town seemed to conspire together to charm her. Everywhere we went, there were people sitting on porches waving and saying “hello,” or old-time string bands on the corner plucking and singing or belting the occasional trumpet solo while passersby danced as if all of this was absolutely normal. And the first bet she ever placed, a $10 win bet on a 30-1 longshot she picked because of its name (Distressed Debt, which spoke to her in a sad kind of way), was a big one. She cashed for $300 her first time to the windows. She put the money in her pocketbook and didn’t bet again the rest of the day. I was disappointed. Could this relationship possibly last?

We traveled down to New Orleans to visit a friend who had recently bought a house there. We did all the usual New Orleans tourist crap, but my friend and I insisted that Katie go with us to the Fair Grounds. She had her heart set on some kind of architectural tour or museum or some other kind of cultural tourist nonsense. I told her that she’d get all the Louisiana culture her heart could desire at the Fair Grounds. She reluctantly agreed.

By this point, she knew what she was signing on for. And, though my track record with women at the racetrack was spotty, I knew that if she was the one, she would have to handle this part of me. I hit a few small bets throughout the day. She barely bet at all. She seemed uninterested. I had to put the jumper cables on this day … and on this relationship. I knew that the best way to get excited about this game was to get some skin in it. I made her take out all the rest of the money she had planned to spend that day. She only produced about $40. I combined it with my $40 and my friend’s $40 and we built a big Pick 3 ticket that, if we could hit, would take us through the end of the day’s card. I put heart and soul into picking that Pick 3. And going into the third leg with a live ticket to two runners, with will-pays in the thousands, I could see that my hard work had paid off. Not because of the money we stood to win, but because Katie was fully invested. She was chatting up strangers around us about her ticket and which horses she had and whether they liked her chances or not. She was smiling, but she was also very nervous, which was exactly where I wanted her. After the race, I suggested we all get lobster.

Oaklawn an ideal venue for a date. (Penelope P. Miller/America's Best Racing)

A few months later, she and I travelled home to meet my family for the holidays, and by holiday I mean the Arkansas Derby. She met the whole clan and spent a couple of days at Oaklawn. We even got dressed up. She didn’t do much gambling, but I did. I managed to win a bundle that day, between a Pick 4 I cashed and a huge exacta on the last race of the day. I threw the money around like a bigshot, paying for dinner and drinks and whatnot. My parents and cousins got sloshed on my tab. They tried to get at my winnings by offering me to shoot dice in the bar. I cleaned them out of everything they had left. How could I lose? I was on a streak.

Katie watched all of this unfold with equal parts horror and curiousity. She was from an uptight Westchester County church-going family. This wasn’t her world, this redneck bar full of drunks fresh out of the racetrack, shooting dice in the corner and telling dirty jokes. But that’s maybe what made her soak it all in, made her want more of it. After all, we can have all we want of our own worlds. We partner up to hopefully broaden our horizons, to add something to ourselves we didn’t even know we were missing. Sometimes we do, anyway. Sometimes opposites attract. Katie came back for the Arkansas Derby the next year. My family liked her a lot. They’d tease me that it made no sense that such a beautiful and intelligent woman would keep company with me. They’d needle me about locking her down. Despite being a lifelong gambler, I finally understood why she put that money in her pocketbook after she won her first ever bet. When you have everything you want, everything you had your heart set on, why keep betting? Lock it up. Go home happy, a winner. When we got married, she let me name the tables after racehorses. She wouldn’t let my cousins play dice at the reception. That’s what love is, folks. Give and take. Win and lose. Going home happy.

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