A calculated risk

It’s been a while since I went on a date. Can’t say there haven’t been a few opportunities, but not really ones I was willing to pursue.

People around me say I play it safe too much, that I won’t enjoy life if I’m always so cautious. They’re not wrong, but they’re not right either. I chose the safer options for major life decisions and I haven’t regretted any such decision so far.

With relationships and hookups however, I admit I often wonder what would’ve happened if I had taken a gamble in some of those cases, but it’s not like those thoughts are keeping me up at night.

Obviously, some mistakes and regrets are unavoidable in life, but if I am to take a risk, I want it to be a calculated risk.

That’s why I’m going to meet this guy I’ve been talking to on Grindr for a few days now. He seems spontaneous and into activities that involve adrenaline, so we might not be that compatible in some areas. But he’s the first in a long while to propose meeting up in a pub in the afternoon instead of one of our places in the evening or at night, so whether he’s looking for a more meaningful connection or he prefers taking things slow, we match in that area at least.

Jason said he’d wait at a table by the window, but this pub has unexpectedly many rooms and tables near windows. So, if he actually looks nothing like his profile picture, finding him is going to be a bit of a hassle... Oh, never mind. There he is.

“Hi. You’re Jason, right? I’m Trevor.”

“Hey. Nice to meet you in real life.”

As he smiles and stands up to shake my hand, I somehow get this odd feeling that we’re about to start a business interview instead of a date. There’s a nearly finished Frappe near a cardboard box on the table, so I assume he’s been here for a while.

“Have you been waiting long? I could’ve also arrived earlier if you had messaged me to let me know you’re here already.”

“It’s fine. The pub only has one poker set that’s not worn out, so I wanted to get here early and book it.”

“So… you wanna play poker?”

“Yeah. I always do this on first dates. If you win, I’ll go out with you.”

Well… this is unexpected… I might have been out the dating game for long enough to not know what the standard practices are anymore, but I’m pretty sure this is unorthodox… And judging by the confident and challenging look in his eyes, he’s not joking around…

“With that kinda wager, it makes it seem like you’re the prize and I’m the one yearning for it. My pride’s objecting. How about the one who wins gets to decide if we’re gonna go out or not?”

“Are you really okay with that? If I win and decide we’re gonna go out, but you’ll find me increasingly unpleasant as we play, you’re really gonna hate the outcome.”

“That’s true… How about going out for only one week?”

“That sounds like a weak commitment, pun intended. I’m not really on board with the idea.”

“Then we’ll revert back to your initial wager proposal.”

“I thought your pride objects to that.”

“My pride isn’t nearly as important to me as the freedom to choose my own fate.”

“On that note, you’re free to stop the game or leave the table at any point.”

“I might do that depending on what you say next. What happens if you win?”

“Well… you’ll find that out if you don’t manage to stop me from winning.”

Look at that cocky smirk and that challenging look in his eyes… This is lightyears away from the calculated risk I thought I was taking. But, somehow…

“I see… Alright, I’m in.”

He seems taken aback by that answer. Can’t blame him, since I’m even taking myself by surprise here… Why am I getting such a rush out of this?

“Cool. You said you know how to play, but let’s go over the rules briefly till our drinks get here.”

So… we’re playing by Texas Holdem rules for two players and we each have 64 $1 chips, 32 $5 chips, 16 $10 chips, 8 $25 chips and 4 $100 chips. This could turn into a long game if we were betting money, but it’s only the overall win or loss that counts, so the betting can get really flexible or even erratic and the game could end in a flash. And he said I’m free to leave the table, so even if I back out when I’m down to my last chip I wouldn’t lose anything. Also, I’m pretty sure he tried to make me unnerved when he avoided saying what would happen if I lost. This guy…

“So, for the first round, I’ll be the dealer and the small blind since I drew the higher card and we’ll switch that up every round.”

“Alright. But, before we start, I wanna ask you something. Do you usually do this on first dates to assess the character of the people you’re considering dating?”

“Oh. You figured that out already? This game’s gonna be fun.”

“What happens if your date doesn’t know how to play poker?”

“I ask them to come to an indoor rock-climbing session with me.”

“Ah, I’m really glad I know how to play poker then.”

“Why?”

“I’m not that strong and I’m afraid of heights. Any kind of rock-climbing would have me sweating in more ways than one.”

“I see. Then, if I win, you’re coming rock-climbing with me.”

“Thought so…”

“Thought so? Did you deliberately give out that information knowing that I’d use it like this?”

“Yup. I really don’t wanna go rock-climbing, but it beats feeling the pressure of an uncertain outcome.”

Judging by that sparkle in his eyes, he loves being challenged. Thought so… How’s he gonna win at poker when he’s this transparent? Oh, right, his goal isn’t really to win…

“I’ll deal the flop now. After that, it’s your turn to fold, check or raise.”

Surprisingly, he didn’t start betting pre-flop. I guess he wants to see what I do first. What should I do though? With the cards in my hand and the three community cards, I already have a pair of tens. After the Turn and River are dealt, my best-case scenario would be Four of a Kind or Full House. I have no chance for a Straight or a Flush, but it’s reasonable to hope for Two Pairs or Three of a Kind. It’s worth betting, but this round will set the tone for the following ones, so how much should I bet? However much I bet, he’ll likely double or triple that to throw me off with his boldness and make me fold. If he sets the pace like that, I’ll go down the slope of folding often and he’ll keep eating away my small bets while also chipping away at my confidence and will… So, I should make a bet I’m ready to triple.

“Raise. 25.”

“Raise. 125.”

This guy…

“Why are you laughing like you just heard the best punchline ever?”

“Let’s just say you have a way of breaking expectations. Call.”

“You’re one to talk… I didn’t expect you to call that.”

“I can’t explain why I did that without giving you too much insight and, thereby, making the game dull. We agreed to one round of betting per cards dealt, so you can deal the Turn now.”

Is a bold first strike his signature-move? Not even a minute into this date, he hits me with a “if you win at poker, I’ll go out with you” and now he does this. Like that, he probably gets a lot of people either backing out early or being carelessly bold, which makes it pretty clear what types of people he doesn’t want to waste time on. So, he’s probably also the type that doesn’t easily back out, which makes me want to stay at the table even more without getting sucked into his pace. For now, I’ll…

“Check.”

“Raise. Another 25. Total of 150.”

“Call.”

Ah, damn, he smirked… Next round he’ll raise so much I’ll either fold or piss my pants while calling…

“I dealt the River. Last round of betting and you’re up.”

Fine, Jason… I’ll go rock-climbing. But I won’t be intimidated by you.

“Raise. 50. Total of 200.”

“Oh, wow… Raise. 100. Total of 250.”

Damn it… He’s brimming with excitement. No wonder he can afford being transparent while playing poker. A storm doesn’t have to be subtle when it hits you either…

“Call.”

“Showdown?”

“I have a pair of tens.”

Why is he chuckling? What does he have?

“Ta-dah!”

“Nothing? You were betting like that with nothing?”

“I was kinda hoping for a Flush, but I’m more satisfied like this.”

“You’re satisfied? After losing over a quarter of the value of your chips?”

“But I’ve gained valuable insight in the process.”

“Like?”

“I can’t play around with you, since you’re too smart and serious for me to do that, but I can enjoy playing against you very much. However, I’ll be conflicted, since I kinda want you to win.”

“You kinda want me to win, huh? What if, after I win, I decide to not go out with you?”

“That’s not an option. If you win, we go out.”

“So, it’s either I go out with you or I go rock-climbing? What if I don’t want either?”

“Then you can leave the table and that’s that. But you won’t leave the table. Either at all or until before the last round of the game. You said earlier that your pride’s not that important, but with how you were betting you were practically shouting “I won’t back off or get intimidated”. I also noticed a few other things, but I can’t reveal them yet.”

“You’re a bit… difficult, aren’t you?”

“I believe the term you’re looking for is “pain-in-the-neck”, right?”

“Let’s not go there… While I shuffle the cards, can you tell me how many people usually turn you down for this kind of first date?”

“Around 60%.”

“Really?”

“Most people don’t adapt well to things that don’t align with their expectations. Most people are also way more cautious than they think they are. What happened since you came and until now is what I do every time. Most people react to that by becoming hesitant, suspicious or offended. Those who decide to play against me usually do it with the intent of putting me in my place. I’m actually looking for a serious relationship and with this kind of context I can evaluate pretty accurately how people approach various things in life. I developed interest in you through our online conversations, so I was kinda sad on my way here because I was almost sure you’d be hesitant about this whole deal, but… I was surprised.”

What’s with that serious look? Seems like you made up your mind that I’m the right kind of person for you, but I wouldn’t be so sure about that…

“Let’s continue the game, shall we? Small blind.”

---

I somewhat expected this. After that first round, I kept having to fold either because of bad hands or because he was raising to a point where I wasn’t willing to match him. There are a few ways out of this, but I want a certain one of those ways. However, for that, I’d need a certain reaction from him.

“You know, Trevor, it’s gonna be hard moving forward if you keep playing so cautiously…”

There it is. Perfect.

“People constantly tell me I’m too cautious and I’m kinda sick of it. It’s not even true anyway.”

Did he buy that bluff at the end? We’ll have to see during the next couple of rounds...

---

“You really played me starting with that bluff about you not being cautious…”

“Oh. You caught onto that?”

“I knew you’re cautious starting with your first bet in this game. I tried taunting you a bit about that to see if you’d make a drastic change in your gameplay, like pulling a daring bluff. It seems like you were counting on me to assume you’d bluff after the taunting, because you waited another round till you got a strong hand to start raising. I matched those raises and ended up losing, but your goal was to show me your strong hand, thereby ingraining it into my mind that you’d only make considerable raises when you have a strong hand. But then, in the next round, you bluffed. Then you bluffed again… Well played.”

“If you were aware of all that, maybe you shouldn’t have bet over half of your chips.”

“I only became aware of the full picture now, in hindsight, and I made those bets because I wanted to see where things were going. It paid off. I got to see a very relevant nuance to your cautiousness. It’s not that you’re not taking risks, it’s just that they’re all calculated risks. And you can pull that off because you trust your own choices and you have the mental strength to follow through with them. So, basically, you do take risks but, when you do it, you think more and waver less. I saw that throughout the game.”

“I did not expect to be psychoanalyzed to this degree on a date, but I do like being understood for once. However, now you know – I’m pretty much the opposite type of person that you’re looking for.”

“I disagree. You’re pretty much the exact type of person that I’m looking for and I am the same.”

What is he… Ah, right, I see now…

“Choosing who you’re gonna date like this is a calculated risk on your part. Everything you just said about my gameplay, also applies to how you carry out your first dates, right?”

That smile pretty much confirms it and that look in his eyes shows that he likes being understood for once too. This guy, really… is such a surprise.

“Your turn to deal the cards.”

---

What should I do? He’s down to his last few chips and it seems like this might be the last round, so I’m not sure how I should bet. Last time we were in this situation, I started betting conservatively to keep the game going, but he took advantage of that and said “If you wanna go rock-climbing that bad, I can arrange it for tomorrow.” with the cheekiest grin ever. Damn… I got so pissed I started betting like crazy. As a result, the most recent rounds have been really intense and huge piles of chips kept going back and forth on the table. I don’t wanna go through that again, so I should either leave the table or try to end the game with this round. Leaving the table is out of the question by this point though. I wanna win for two reasons: a sense of victory and going out with him. He kept saying he wants me to win, meaning he still wants to go out with me, but this guy… has been playing like he wants the exact opposite…

“Earth to Trevor. Are you gonna bet today?”

“Hold up. I’m a bit conflicted over here.”

“What are you conflicted about?”

“I wanna bet the amount of chips that you have so you’ll have to go All-In, which you will because you haven’t folded even once in this entire game. But, judging by the community cards, there’s a chance of you ending up with a Straight Flush, so you’d win the round and, with the amount of chips you’ll then have, it’ll take even longer to beat you. But if I make small bets, it’ll also prolong the game indefinitely and I wanna win already so we can get to the next stage and start going out. That’s why I’m conflicted.”

“Oh… You finally admitted that you also want to go out with me.”

“Hasn’t it become obvious along the way?”

“It has, but I still hoped you would also say it out loud.”

It’s gonna get really hard to continue thinking straight if he looks and smiles at me like that, so…

“Raise. From now on, I’m betting the exact amount of chips that you have so you can go All-In. At some point, I’ll have a higher hand than you do and, like this, the game will end sooner. If I end up losing rounds one after the other and then I’ll end up rock-climbing, so be it. I’m taking the risk.”

“I like how you decided to approach this. All-In.”

“Showdown. I have one pair of Kings.”

“I have – ta-dah – nothing again.”

“What? Wait, something feels off about this.”

I was sure he switched one of his cards with one of the burnt ones, but when I wanted to grab them and check, his hand came over mine to stop me and the sensation resulting from that touch was like an electrical current that caused a temporary short-circuit in my mind.

“This’ll be my first and last time cheating in our relationship, so how about letting it go? I’ve reached the limit of my patience and I’m hungry as a wolf, so how about going for dinner somewhere?”

“Sure. Would you like to come to my place afterwards?”

“We’re going All-In already?”

“Well, I’m pretty confident in what I have in my hand this time.”

By that, I mean his hand that I started holding on the table and, by the soft squeeze it gave me, I can tell he feels the same.