Who's never been on holiday with a friend before?
Went on vacation to a resort with a friend 10 years ago, and it was just plain horrible! He quickly met people who were "more normal" than me, and not only left me out in the cold, but joined them in pranking me. I kicked his ass to the curb the minute we got off the plane in the airport back home, and haven't spoken to him again since. I've also gone with other friends on weekend trips (which I don't consider to be true vacations), and those ranged from "so-so" to "pretty nice". But even then, we did many things they wanted and only one or two things I wanted. My friends are more socially dominant than me, so that was bound to happen, and I set my expectations accordingly. Example: one time when we went camping (which in and of itself was kind of nice), I wanted to go into town to a bar in the evening; I even said I'd drive. My friends wanted to sit around the campfire and meditate. What did we do? Meditate. Well, they did it, smiling blissfully. I just chain-smoked cigarettes, bored out of my mind; I couldn't even look at stars to entertain myself, because they were obscured by trees.
Ironically, my truly best vacation was a cruise that I went on by myself. (The cruise community prefers uses the term "solo".) I loved the complete freedom of doing whatever I wanted and not having to compromise with anyone! There were tons of activities to do on the ship and in ports, things like dance classes, nightly shows (mostly vaudeville-type), fun demonstrations, art auctions with free drinks, and a deep blue ocean to just stare at from the top deck. Finding people to eat with was not a problem: dinner had assigned seating, so I had a guaranteed group of people to eat with, and other meals were fine, since eating alone on a cruise ship is seen as normal, as opposed to "embarrassing" or "pathetic", like in most American suburbs (city centers are more "lenient" on eating alone). Boredom never even entered my mind, and lonely moments were very few and far between. I made friends with a few other passengers, practiced my Spanish with crew members who spoke it, and even got a woman romantically interested in me. I did not have a single experience that ruined my cruise; any downers that did happen were insignificant, like not getting to the orange creme cake in the dining room.
What will the future hold? No clue. My stories got a lot of my friends interested in cruising, and they said they want to go with me next time I go. But that's where my hesitation sets in. On one hand, it could easily be a fun vacation and a great way to hang out together. On the other hand, they're more socially dominant than me (although interestingly, I was able to get a conga line of 20 people to all break into a song), so they could use that to drown out my wants, and we'll end up doing only the things they like. Given how short most cruise vacations are, it's often a "one or the other" kind of thing. On a solo cruise, that's obviously not an issue; the only person whose wishes are taken into account is you. Yes, I'm selfish like that , but consider my past experiences with going on vacations with friends, it's not unreasonable to have reservations about doing it again.
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