Asking A Boy Out

I’m writing to you all in a state of panic. I have the total hots for this upperclassman, Charlie, and my feelings for him have only gotten stronger since we began talking at the start of summer break. Although I know that we’ve discussed the prospect of going out on a second date, and have had conversations that have stretched over hours, I can’t help but feel as though I still don’t hold his interest. There will be little spurts where he pays me a flirty compliment, or implies a slight crush, but I can’t help but look for subtext in every text he sends. It’s almost as though my brain doesn’t want him to like me back.

Needless to say, it’s very frustrating– especially when we had been talking about a comedy show that I had went to a few nights ago. I had asked him if he’d ever seen stand up live, and when he told me he hadn’t, I decided to say, “Then we should totally go to show when I’m in town!”

“I’d love to!” He responded.

That seems enthusiastic, right? Of course not! “I’d love to” was perhaps a default answer to a date he doesn’t think I’d follow through with. It’s easy to say yes when the plan isn’t concrete. He probably didn’t want to see me at all, and was just letting me down easy.

Relax, Eloise. Relax.

Some time went by and I found out that I’d be in his hometown to spend Fourth of July weekend with some friends. I had already asked him if he was doing anything special for that weekend, and when he assured me that he wasn’t, I took that as an opportunity to ask if he was free the fifth.

Thus the panic ensued. A few hours later, I went on Snapchat (Gen Z-ers favorite platform for budding relationships) to see that he had opened my message four minutes before. Still no reply. It doesn’t take four minutes to answer with a yes or no. What could he have been waiting for?

My stomach was twisting and I couldn’t get my brain to stop thinking. Six minutes… eight minutes… ten minutes… twelve minutes… nothing.

I ruined it. He doesn’t like me. He doesn’t want to go out with me. He’s thinking of excuses–

Ding! New message from Charlie Stetson.

That brings us to now. I still haven’t opened it, and I’ve decided I’d capture my raw insecurities at the height of my distress. I’m trying to prepare myself for whatever excuse he gives. I’m trying to convince myself it’ll be okay if he doesn’t want to see me. Not feeling good enough is so hard. It feels like my whole body is sinking and I don’t know why.

It’s dramatic and very teenager of me to feel this strongly about a boy, but it’s not necessarily him that I’m afraid of losing, but my confidence. I’ve been trying to work my self-esteem up to be in a place where I feel like I deserve the good things in my life that I’ve been getting, so I’m just scared that his rejection will make me question if all this work I’ve put into myself has been worth it. If I can so easily be set back, have I been taking the wrong approach towards being more comfortable in my own skin? Is being hurt by rejection part of process, or proof that I’ll forever be stuck with “not-feeling-good-enough”s? What is the correct way of going about this and how do I know if I’m on the right track?

For the past 20 minutes I’ve been trying to accept that part of asking someone out is being okay with whatever answer they give me. The fact that I allowed myself to be so vulnerable means to some extent I have subconsciously grappled with the pros and cons enough to have made this choice. I need to trust my instincts.

I’m going to open it. I’m ready to open it. I unlock my phone and open Snapchat. Inhale. Tap.

A picture of him covers my screen and my eyes linger on his face– the familiar blonde curly hair and wide-framed glasses. His smile is always gentle, welcoming, and warm in photographs, and here is no different. The photo is captioned with a: “Yes! I’m totally free.”


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