Also agree with the other great suggestions in the sibling comments.

One thing that would help if you could figure out the types of games you and your group might enjoy — or the type of group you and your friends are.

If you think you’d enjoy deeper strategy games, start with some of the popular games in the “strategy” category on BGG, looking for light to medium weight (1.5-2.5) to start out, working your way up the scale (to 3.0, 3.5, and 4.0).

If you’re more into the social/party type games (those are always more fun in larger groups), look at the party category. I particularly enjoy social deduction games in the right group, and those are usually big hits with older kids / younger adults (though I still enjoy social deduction games and I’m quite beyond “younger adult”). :)

One good example is One Night Ultimate Werewolf.

One tip: if you’re interested in trying out some strategy games that are a bit out of your price range, check out boardgameoracle.com and add price alerts on a few games you have your eye on. Many great board game sites run good deals (gamenerdz.com is one of my favorites), so you can often get good deals on games if you’re patient.

If you ever get to the point where you’re looking for something with a bit more depth, and are ok spending money, but you want the money to go a long way, Age of Steam is one of the best bangs for your buck.

It’s basically a system that has a library of probably close to 200 maps, where each map can change the game quite drastically, by tweaking several rules, in addition to a different map of course.

It’s currently my #1 game, and you could repeat plays with it without it getting old, assuming others enjoy the mechanics of game (route building, auction/bidding, tight economy).