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I go on a lot of family vacations – ski trips during the winter, week-long beach getaways in the summer, pumpkin picking upstate in the fall (what can I say, we’re kind of corny). So it was only inevitable that I would one day bring a boyfriend on vacay with my big, messy, disorganized family. And that day just happened to occur a lot sooner than I thought it would – when I was 16-years-old.

I had been dating my boyfriend, D, for over a year when the time came for my fam to start planning our annual skip trip. Even though I was looking forward to it, the idea of spending a full week away from D made me cry (literally – I’m a huge crier). I begged and begged my parents, and finally, after weeks of pleading, bribing and sobbing, I got my way: I could invite D to come with us!

The thought of being able to spend an entire week with my boyfriend was SUPER exciting. I couldn’t wait to spend every minute with him and have him get closer to my beloved family. I didn’t once stop to consider the potentially awkward moments that this could bring: where would he sleep? How could we possibly hook up while my parents were always around? What would happen if we got in a fight? We had never spent seven straight days together – what if we got sick of each other?

It wasn’t until I got there that I thought of all these things. And, um, yeah… it was pretty awkward.

My parents obviously wouldn’t let D and I sleep in the same bed, so instead, they blew up an air mattress and forced my little brother to sleep in the living room with him (I think my brother was supposed to babysit us just in case I wanted to sneak out of my bedroom in the middle of the night). When I woke up the first morning, in my glasses, old pajamas and crazy-looking bedhead, I practically had a panic attack wondering how to make it from my bed to the bathroom without D spotting me.

Hooking up proved to be super difficult – my parents, grandparents, aunts and uncles seemed to be watching our every move. My cousins and siblings didn’t go to sleep until well past midnight, and I’m pretty sure my parents got zero sleep since they spent the majority of their night checking on us.

As expected, D and I got in a few small fights, and those were the worst. Try getting into an argument with your boyfriend while on a ski lift, only to angrily get to the bottom of the mountain and then take a 45-minute drive with him and your whole family stuck in one little car. Or try pretending not to cry in front of your grandma while your BF furiously texts you from across a hotel room. It sucks. Trust me.

By the end of the week, the seemingly impossible had happened: I was kind of getting a little sick of my BF. For me, family vacations had always meant sleeping late, joking around with my cousins, reading a new book and just generally relaxing. Now, I had this dude with me who kind of demanded all my attention. I had to compromise my vacation time, and honestly? I was kind of bummed about it.

I feel like I learned a lot from that vacation. I realized that sometimes it’s a good thing to spend a few days away from your boyfriend. I also realized that while I love bringing friends and/or boyfriends away with my family and me, I also love having vacay alone time – and quality time with my fam.

Have you ever brought a boyfriend/girlfriend on a family vacation? What was it like? Would you ever do it? Tell me in the comments!

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