One of the greatest things about Boston, in my opinon, is its eclectic bar scene. Delve into the diviest of dives in Cambridge, relax in a trendy gastropub in Allston, get down and dirty in a dance club in back bay, or pass pitchers while you shoot hoops in Fenway. The diversity of options is tremendous. Wish I could say the same about the guys. Depending on where you choose to spend your night on the town, you will definitely find yourself surrounded with at least one, if not all, of these typical Bostonian guys.
PS: Don't let this list deter you from checking out the bar scene in the lost hopes of finding the Ross to your Rachel - this is just a list of the typical guys you'll meet at a Boston bar. It's the not-so-typical ones you want to get your hands on...and they're out there...if you look hard enough...maybe.
The Once a Frat Bro, Always a Frat Bro
Who they are: Usually between the age of 21 (or younger if they have a quality fake) and 26, these guys are all about partying, either because they are still in school...or just stuck in that college-life mentality. They will be the ones ordering tequila shots at the bar, taking their shirt off in the middle of the dance floor, and stumbling down the cobblestone streets of Boston. Oh, and you can probably expect a sext from them at some point before the nights over. Possibly while still on the dance floor.
Where you'll find them: Beacon Hill Pub, Stats, Coogans
The Clichéd Hipster
Who they are: If you find yourself in Allston, the Hipster variety will scale on the younger end, around 21-24. Move over to the Cambridge/Somerville area, the age jumps a little higher, maybe 23-30. You'll know you've spotted one if you catch glimpse of a thick beard, a beanie, and hear any mention of gluten-free, artisanal coffee, or rock climbing.
Where you'll find them: Great Scott, Deep Ellum, Trina's Starlite Lounge
The D-Bag Professional
Who they are: They're definitely not from Boston, but they've been living here for a while. They take their stable, office job very seriously...but they are working for the weekends. Aged 25-32, you'll recognize these guys standing in groups by the bar; tucked in button-downs, pressed khaki pants, and probably boat shoes. They look good...and they know it (eye roll). The tricky thing about the professionals; it's hard to distinguish the normal ones from the d-bags. Once they start talking about their job or money, run away.
Where you'll find them: Harvard Gardens, Lolita, Legal Harborside
The Persistent Foreigner
Who they are: Probably somewhere between 21-28, these guys usually come from money and are used to the international club-esque party scene - an area where Boston definitely falls short. This is why you'll find the Foreigners flocking to the few "clubs" Boston has to offer. Their incessant desire to dance can sometimes come off as creepy. But they'll definitely buy you a drink.
Where you'll find them: Whiskey Saignon, Royale, Estate, Howl at the Moon
The Sugar Daddy
Who they are: A bit older than most of the other guys you'll see in Boston bars, these men range between 35-50+. They're single (or so they say), and have their eyes on the prowl for a girl who might be interested in a couple of free drinks that could lead to...well, whatever that may lead to. No judgement.
Where you'll find them: The Liberty Hotel, Gaslight, Cuchi Cuchi
The Wicked Townie
Who they are: These guys are Boston born and bred (or somewhere right outside of Boston). You'll quickly be able to identify them as soon as they open their mouth; the accent is unmissable. You see them and instantly think, "Good Will Hunting." These guys range in age from old to young, and stick to the dive bars they've been going to for years. Often conversing about the Pats, the Bs, the Sox...or any other Boston sport related topic, they typically keep to themselves.
Where you'll find them: Courtside, The Corner Pub, Old Sully's
The Insufferable Scholar
Who they are: Students of MIT or Harvard, these males are smart (nerdy, if you will), focused, and err on the side of downright arrogant. They usually have a solid chunk of change saved up (whether that be thanks to a trust fund or not), but don't think that means they'll be doling out drinks. You'll likely find them speaking with another Scholar, robustly discussing some nonsensical new discovery while sipping fine wine...and they're probably wearing a scarf.
Where you'll find them: Cambridge Queen's Head, Grendel's, Deadalus