11 June, 2015

Ask A Guy: The First Holiday – What You Need To Know

11 June, 2015

Welcome to Ask A Guy, where you can find unfiltered, honest, feedback on how guys (well at least one: me) really think about things, from relationships to body types to life dilemmas. Here’s this week’s:

Question: I’ve been seeing Tim for a month and it’s going well. He asked me to come to Bali with him for five days. I’m kind of nervous. Should I be? What do I need to know?

You’re nervous – duh. First vacations are a rite of any relationship along with meeting the parents and the first pregnancy scare. What if you don’t like each other? What if he’s a psycho and you’re trapped in a remote villa where nobody can hear you scream? What if you don’t pack the cute swimsuit, but instead the one that used to be cute? We’re truly dealing with some important life questions here.

There are three things you need to know about going on the first vacation together and only three:

1. Are you guys Planners or Chillers?

Holidayers break nicely into these two categories. Planners plan things. They know where to go in the spot you’re visiting and are excited to check out the temples/Michelin star restaurants/secret waterfalls. Chillers think that vacations are all about being unplanned. Work is already so structured that on their break they’ll do what they feel like at the time. If they’re hungover, they’ll skip that hike and snooze during the day. To a planner, this is akin to saying, “You are dumb and I don’t value the immeasurable work you’ve put into this holiday. You suck.”

So make sure beforehand that you know which one each of you are. If you’re both chillers, chill. Easy. If you’re both planners, plan beforehand. It’s a couples activity and you won’t end up with duelling itineraries. If you’re a chiller and he’s a planner, think of him as a tour guide you can kiss and do stuff with. If you’re a planner and he’s a chiller then you’ll have to chill out. Suggest the plan, but if he says he doesn’t want to or is tired, roll with it. Dragging him to something he’ll grumble at will make the experience suck for both of you.

ask a guy the first holiday

2. Three Strikes for Weirdness

Everyone is weird (I know, weird fact right?). But on holiday, it really comes out. So you have to give him three strikes, even if it annoys you. This is only for the holiday – you’ll learn to love his quirks or he’ll learn to change, but this can only be discussed when you’re further along in the relationship. If he sits on the bed with his shoes on, ignore it! Call down when he’s not listening and tell them to change the comforter while you’re out. If he leaves the bathroom light on, turn it off and don’t say anything. I’m not telling you to be a huge pushover; I’m just saying give it a little time. But he only gets three chances. If he keeps doing dumb stuff, yell at him or maybe just get out of there.

3. Accept your Fight

Go into the vacation with the understanding that you’ll have a fight. That’s ok. It means there’s passion in the relationship. If you guys don’t – awesome; you really like each other. Or, you’re really passive-aggressive and I’m sure you’ll have a really good relationship. The timetable for your fight:

  • Day 1: Show up. Be excited you’re there. Jump on your hotel bed. Laugh. Kiss.
  • Day 2: Spend the day exploring where you are. Eat good food. Be happy you’re not at work. Kiss.
  • Days 3-7: Wait. I have to spend the rest of this holiday with someone who clipped his toenails in front of me and left the bits on the side table????

You guys are getting to know each other. That’s cool. So it’s natural you won’t understand everything right away. And you might quibble. But don’t explode. When the fight comes let it wash over you, express frustration, make-up from your fight, and do things people on holidays doing make-up things should do.


And if you survive the holiday, congrats yo. You might even be ready for a real relationship.

Image #2 via Pinterest

Back to top