If you're healthy about it and comfortable, I think sharing a drink between friends is a great way to get to know classmates, coworkers, and the like. So when I turned 21, I was very excited to finally drink with my family.
You get older and you start learning family stories that you weren't allowed to know when you were a kid and you realize your family has been through some shit. Everyone starts getting closer because everyone's conversations feel more real, now.
The two halves of my divorced family are drastically different. On one side, everyone's Jewish and loud and very interested in every little detail of your life, even if you're not super willing to share, but they, of course, mean well. On the other side, everyone's obnoxiously competitive but very private about details going on in their lives. They push buttons in good fun, while the Jewish side pushes buttons because they just wanna know! Why is it a big deal? It's just your VAGINA. That side of the family showed me a cartoon drawing of a penis in a library book when I was 5 because IT'S JUST A BODY PART! STOP OVERREACTING, [insert name of mother from the personal space-conscientious side of the family, here].
My dad this year turned 50, and he threw a bash at a bar downtown for the occasion, so I got drunk with the loud-half of my family, first. This wasn't a surprise to me seeing as they're more party-oriented. Dad rented out a space with live-band karaoke, Jello shots, and complimentary wine for the night.
My dad and I bet who would puke that night, me (newly 21) or him (trained in drinking for at least 30 years). He said I would and I said he would.
He puked in the Uber on the way home. I won.
Drinking with the other half of my family was a different occasion. I hosted Thanksgiving at my small college apartment this year to better the chances of other college cousins being able to drive in from where they were instead of all the way home. I had Great Lakes Christmas Ales ready, board games, and all the ingredients I was sure my family would fall in love with.
Like the way this normally goes, I was the obnoxious kid in the family who was nothing like the rest of us. It was cute that I had board games available, but no one drank more than a single beer with me (I had like 4, and Christmas Ales get you good). And I introduced the family to a new board game that I tried to explain to them, drunk.
Explaining how to do things drunk is difficult for anyone. But to my family, who will make 27 jokes per minute along the way, it was quite the frustration.
In the end, the game was a winner and my family agreed to play it again in the future with more of us! I, however, will be known on one side of the family as the holds-her-liquor, karaoke-driven, fun drunk, and the other side as the crying, pushy, and fights-back drunk.
The lesson at the end of the day is, before you drink with your family, maybe ask yourself which uncle is telling you cute stories about your father in college to relate to while you're drunk in front of him for the first time, and which uncle is asking, "She cries when she's drunk?! Aw, well let's make her cry! Get her another beer!" before you decide to make that first toast. ;)