30 tinder Dates in 30 Nights – {Date 1} The Gambler

My first date of the month was fun. He had mentioned to me during our Tinder chats that he plays tennis often and asked if I would want to play on our first date? I nervously agreed, knowing I’m terrible at the game, but I do enjoy it once in a while. Still, I was looking forward to meeting him, he looked cute in his profile photos, and I especially liked the one with his grandfather.

I sent Tony a picture of my date with a few details about him. Tony replied with some advice, including:

“Ask him what else he likes to do in his spare time and don’t be so quick to judge him just because of what he does for a living.”

Ok, Tony, I’ll try my best!

The Date… 

We meet at the tennis courts. The weather is perfect, sunny and 70 degrees, I love fall! I show up with my super old school tennis racket that I’ve had since high school, and he’s waiting for me with an extra bottle of water and tennis racket. “How thoughtful! Wonder how he knew I’d bring a shitty racket?”, I  think to myself. He has a nice smile, and is very eager to teach me what he’s learned after decades of playing. I’m very nervous that he’ll sprint out after my first serve.

We hit around a bit and I successfully show him how good I am at missing the ball. We laugh, he’s kind about my lack of athleticism, only making a joke here and there. Eventually we take a water break. Excellent opportunity to get to know him better. He tells me that he turned 30 two days ago, and has been celebrating ever since. He works at his family’s business, managing day-today operations, which keeps him busy but also gives him flexible hours. He tells me he dropped out of college after two-years. My first red flag, I have a hard time feeling sorry for young, able-bodied guys with rich parents who drop out of college. But I remember Tony’s advice and decide maybe there’s a good story behind his decision. Oh and there is…

He pulls out an electronic cigarette from his tennis bag, and I ask: “Oh are you trying to quit smoking?” “Hell no”, he replies. “This isn’t nicotine” pointing at the glass tube inside the cigarette. “I bought it from a friend who has a prescription and lives in California.” So here we are, taking a water break, and this guy just pulls out his special cigarette on the first date?! I’m so speechless that all I can do is laugh nervously. “What you don’t smoke?” He asks with a “judgy” look on his face. “You’re Latina right? You should know all about the mota!” I shoot him my meanest look possible and say: “I think I’m supposed to be insulted by that.” And then I laugh, because I decide he’s probably just joking. “I’m sorry he says, I’m coming off my antidepressants because see, I used to have a gambling problem.” Ok! Stop everything! I can no longer hide my look of bewilderment. “You must be joking, you’re messing with me right?” I say to him. “No, I can be serious sometimes.” he answers.

He tells me a sad tale about how his ex-girlfriend sort of led him to gamble away all of his savings, plus the money his parents had given him. By the time he finishes the story it becomes clear why he dropped out of college. The gambling, the green, and a habit of blaming others for his mistakes… yep it all adds up here. I feel bad for judging him, because I think he’s trying to make up for his past indiscretions, he seems to be working hard now, but then I ask him the question:

What are the three things that you would NEVER change about yourself? To which he replies:

“My nose.”

“My “activities”.” Meaning playing tennis, golf and smoking…

“My” religion and personality.

He says that his previous girlfriends told him he talked too much and had no filter. “Some people think I’m annoying, because I say what’s on my mind, but that’s who I am and I don’t care. Am I annoying you?” He asks. Shit! I’m trapped, no matter how I answer I lose. “No, you’re ok.” I reply (lie).

We finish a couple more games and walk to the nearest coffee shop, where he buys me some cold tea. We sit and chat a little longer. I sip my tea listening to him complain about the poor service at this shop, and trying my best to find some more redeeming qualities in him, but he’s just too immature and frankly, a bit of a basket case for my taste. I’m not a fixer of men. I’ve tried that before and it never works. He confesses that he would like to hang out with me again. “You’re cool, I would totally hang out with you again.” He says, almost like he would be doing me a service. “Thanks!” I reply… “I had fun playing tennis.” And I leave it at that.



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