Getting Back In The Game: Planning The Proposal

Eric’s largest piece of luggage lay open in front of him as he sat on the edge of his bed, absentmindedly tossing socks into it. He’d been trying and failing to pack for the last week, and with the flight scheduled for the next morning, he had decided to work from home to ensure he was all packed and ready in time.

“How do you even pack for a ten-day trip?” He asked himself as he stuffed flip flops into a side pocket of his bag. “I’m going to need my Nikes for walking around, nice shoes for dinner, and sandals for the beach. Plus my nice jacket and slacks for this five-star restaurant right on the coast that I’m going to be too nervous to even eat at.” He shook his head, knowing that it wasn’t the packing that was stressing him out. It was something else. Something small, shiny, and at the moment, hidden in the top shelf of his closet.

He wanted to walk over and grab it, look at it, hold it up to the light, as he’d been doing pretty much every time Alyssa wasn’t around, but he restrained himself. He needed to focus. But not on packing. He grabbed his phone off the bed beside him and texted the group chat.

Eric [12:13pm]: Guys I’m max stressing about this proposal. I wanted to do it after our super fancy dinner on the beach, but that’s not until night 3 and there’s no way I’m going to be able to keep my cool until then.

Andrew [12:19pm]: Yeah that shit sounds hella stressful. Why don’t you get it out of the way night one?

Jack [12:24pm]: Or even better, just propose tonight so you can both go into the vacation relaxed and she won’t breakup with you after your crazy travel self comes out.

Andrew [12:26pm]: Oh shit, that’s true. Remember when he slept in the car on Spring Break because he thought he saw a bedbug in the motel bed? Imagine all that anxiety on steroids.

Eric [12:28pm]: Fuck y’all. First of all, I’m a joy to travel with. Second of all, YOU ALL GOT BIT BY BEDBUGS THAT NIGHT.

Eric [12:28pm]: And I don’t want to propose at home, the whole point was to do it in Italy on this fucking picturesque coast. And we’re both going to be cranky and jetlagged night one and I don’t want to fall asleep during the after-proposal sex.

Jack [12:29pm]: Oh yeah lol. That motel was disgusting. You’re still a bitch for sleeping in the car though.

Kyle [12:31pm]: Wait you’re proposing in Italy? How are you going to get the ring there?

Eric [12:38pm]: Kyle, what?

Jack [12:41pm]: Kyle do you legit have Alzheimer’s? I’m worried about you buddy.

Andrew [12:48pm]: Don’t listen to him, Kyle. I respect your commitment to never paying attention when Eric talks. I wish I could have heard less about this damn Italy proposal.

Kyle [12:51pm]: Lol I should probably smoke less. But yeah are you shipping the ring to your hotel or what?

Eric [12:55pm]: Why the fuck would I ship the single most expensive thing I own to some random hotel in Italy? If you think I’m taking this thing out of my pocket for even 30 seconds you’re out of your mind.

Jack [12:59pm]: Well, I hope you enjoy lying to customs about the worth of what you’re carrying. I’m pretty sure you can’t bring anything over $10k through without filling out more paperwork.

Eric [1:11pm]: Ok, I Googled it and I’m pretty sure this is one of those fake rules everyone just ignores. Everyone brings their engagement rings on vacation.

Kyle [1:14pm]: You should smuggle it in your ass just to be sure.

Jack laughed at “You should smuggle it in your ass just to be sure.”

Andrew laughed at “You should smuggle it in your ass just to be sure.”

Eric [1:16pm]: Fuck you guys. I’m going to keep it my zipper pocket of my shorts. I don’t trust Alyssa not to go through my bag trying to find extra space for her stuff because she’s physically incapable of packing light.

Jack [1:21pm]: You’re gonna carry it through security?

Andrew [1:21pm]: What’s the plan when you get to the hotel room?

Eric [1:22pm]: Idk, that’s what stressing me out. I can’t put it in the safe without it being obvious, but I’m not leaving it in my luggage for anyone to steal. I think I’m just going to keep it with me at all times even if it’ll be stressful.

Kyle [1:28pm]: Idk dude when I was in Italy everyone said to be really careful of pickpockets. Plus, a ring box in your pocket is pretty damn obvious.

Eric [1:33pm]: Shit, I was just gonna have the ring in like a little bag and keep it in a zipper pocket, but I’m not trying to play around with pick pockets. Fuuuuck.

Jack [2:01pm]: Dude, you’re way overthinking this. When you get to the hotel room, just wait for her to go to the bathroom and put the ring and y’alls passports in the safe. She’ll be glad her passport is secure, and she won’t question it or need to get in there.

Jack [2:02pm]: And WORST case scenario, she’s super nosy because you’re an awful liar and finds out, and you have to propose in your gorgeous hotel room on the Amalfi Coast. You’re gonna be fine. Stop worrying about how it’ll happen and just worry about what to do when she says no.

Eric [2:05pm]: Lol you fucking asshole. But fair enough. It’ll work itself out.

Dropping the phone back onto the bed beside him, Eric stood and took a deep breath. He walked over the closet to grab more clothes when he paused and looked at the shelf above him. “Ehh one more look won’t hurt.” He thought as he reached up for the felt box.


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