Showing Your Cards When Dating

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Photo by Huy Phan on Unsplash

Hey Kirstie,

I’m 28, single, living abroad, and feel like I’m in way over my head. I recently started hanging out with this girl — of whom I was introduced through a mutual friend — and I’m scared I’m fucking it up.

She’s a great chick. We’re the same age and that’s pretty hard to find, given that we both live on a Caribbean island and the average age for foreigners here is 55.

We’ve been on several dates now. On one of them I went over to her place, which is her parent’s house, and we saw some puppies her family was fostering. Her step-mom ended up coming home early and I stuck around for dinner. I met her whole family and it was a lot of fun.

But yesterday, I had her come over to my place so I could cook dinner. I bragged about my chef skills and opted to make a chicken piccata for her. Well, it ended up taking four hours and I had to resort to Plan B which was grilled cheeses. That sucked but for some reason, I just felt totally off my game. I am known with my friends to be goofy and clumsy. I know for a fact myself that I am indeed goofy and clumsy. And I could tell how incredibly goofy and clumsy I was being with her. And I can’t help but think that she thinks I’m a weirdo.

She mentioned that she loved hanging out, that whenever it was silent with us, she always felt comfortable. She said she felt a connection, but I’ll be honest that we were both stoned and tipsy at this point. It’s hard to remember the convo word for word.

What I’m wondering is, does she actually like me as more than a friend? Does she think I’m trying too hard? And if I reach out to keep trying to hangout, am I showing my cards too soon?

I don’t want her to think I like her too much and that I’m pushing for something too soon. But I feel so worried because I’ve only liked a girl this much once in my life, and she totally broke my heart. I guess I really like this girl and feel totally fucked.

What should I do?


My Cards Are Showing

Dear My Cards Are Showing,

Hold up. Hold up. Hold up. You like a girl a lot and feel “fucked”?

Let’s unpack that for a second here.

Why is it that you believe liking a girl a lot equates to something terrible? I assume you’re feeling like maybe she won’t reciprocate your feelings; perhaps she might one day break your heart.

I mean, I get it. When you like someone, it’s scary to know that person has so much control over your feelings. But feeling totally “fucked”? Now that’s another story.

Perhaps when you were a kid, you had something happen where you liked little Ashley and tried to hold her hand or always tried to be on her team for tag. Then one day, she suddenly began running away from you claiming your cooties would be her demise. Perhaps that created a notion for you that showing interest too early would scare people off.

You talked about your ex-girlfriend having broken your heart too; it’s safe to say that’s playing a part in your current predicament; though, you did get to the point of her being your girlfriend. So however you formed the relationship seemed to work pretty well.

It’s traumas like these that form our ideas about dating. Emotions are a scary thing, indeed. We put them out there only to have them lovingly accepted or trampled on like the black blobs you see on the sidewalk that we are told was once bubblegum.

But then there are the beautiful moments where two people come together, and it’s so romantic you almost want to puke your brains out a little. The couple that seems so content; so much each other’s best friends; so Instagram worthy.

So let’s get to why we’re here: does this girl like you and what should your next move be?

What I won’t do is sit here and tell you I know what this girl is thinking. I’m not a mind-reader; though if I were, my advice column would most likely be the most successful one out there (I’m looking at you Hello Polly and former Dear Sugar).

But what I will give you is some outside perspective. Because when you’re the one that’s in the thick of the emotions, it’s hard to see things clearly. You’re metaphorically treading water; I’m metaphorically watching you from a cozy lifeboat, sipping on my oat milk latte, observing your every desperate kick.

You’re up in your head, My Cards Are Showing. You’re thinking way too much about everything, and if you don’t stop, you may just start to self-sabotage.

Nothing you told me in your story talks about the girl’s actions indicating that she doesn’t like you. But, everything you said was just what you were thinking/worrying about. You assumed her thoughts because of your own insecurities. And that’s an annoying thing about the human condition, we project that shit onto people around us.

To say it’s common for people to see their own worries in other people is an understatement. And I think that’s what’s happening here.

Now, we need to address the biggest elephant in the room. You’re talking about the relationship between you and this girl like it’s a game. Um, hello? We are in 2019. Have you read anything about modern dating? Games are old-school. Waiting to text is lame. Being scared to show your cards too soon is petty.

It sounds like you really, really, reallyyyyyy like this chick. So why in the world are you trying to hide that? What it sounds like is you’re seeking advice on how to play it “cool” but, as you stated, “goofy” is in your character.

I’d suggest you stop trying to hide your emotions. Stop living up in your head. And start just being yourself and, when you think the time is right, let this girl know how you feel. Heck, I’d even say do it sooner than later. I’d prefer to know if someone thought I was simply a friend rather than wait months when I’m deeply invested, emotions are gnarled into it all, and then be flat out rejected. That would suck. A lot. I suggest you DON’T DO THAT.

You sound like a genuinely good guy. I mean, you wrote into me for advice instead of texting some bro-y group chat where I could only imagine the response being something like:

You: “Hey guys, I really like this chick but Idk if she likes me back. What should I do?”

Bro 1: “Did you try fucking her yet?”

Bro 2: “Damn bro.. don’t be such a pussy”

Bro 3: “Ignore her for a couple of weeks.. that always works”

Bro 1: “Down for some Fortnite?”

Bro 3: “Hopping on now”

Please use this emotional intelligence and awareness that you have for the better. Do not run from your feelings. Do not play games. Show your cards, even if just a bit.

I know it’s scary, but what can come from being vulnerable is finding a deep connection with an amazing person. And that’s pretty hard to find in this scary, chaotic, messy world. Even more so when you’re living amongst retirees in the Caribbean.

With Love,


Write in and potentially be featured with my chaotic, well-intentioned advice to

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