Guild Wars 2

I started a few months after a friend of mine and thought that I picked the server he was on. I was wondering if one of us could guest on the others server, or if we could force ourselves into an overflow

You can guest to other servers. I’ve included an image below to help you. When your friend is online, an icon will show you what worlds you have friends on, so that’ll help you pick it out easily. If you play together the majority of the time, you can also transfer to his server for a fee to skip the minor hassle, but guesting is a good, easy solution.

I thought you couod only guest for 24 hours

You can guest on up to two servers within a 24-hour period, but you can spend as long as you like on a guested server, and guest there as often as you like. It’s not a problem.

If both of you just started and haven’t gotten too attached with your characters, one of you might consider deleting all your characters and moving servers. Not being on the same server prevents you from playing World vs World with each other.