6 Types of Island Boys 

When you live on a very small island, your options for dating, casual hookups, or serious relationships are also very small. You quickly learn that there are a handful of different “types” of these island boys and what it all means for us single island girls. Through personal experience, the coconut telegraph, and hilarious stories from my girlfriends, I came up with 6 types of island boys. To any of my friends who may loosely fit onto this list…don’t take this seriously. You know we love you. 

1. The Charming Bartender 

Every girl does have or has had a crush on one of them. They literally make their living off of their amazing social skills and they get you drunk professionally. The Charming Bartender learns your name quickly and remembers the things you tell them during your cheap, knock-off therapy session at happy hour. They are the flirts, they are witty and sarcastic, and they will charm your pants off but remember ladies, you are not the only girl at his bar. Before you confess your love, talk to him when his shift is over and see if he pays as much attention to you when you’re not…paying him. 

2. The Boat Captain  

If he works on a boat, you’ll know it within the first 30 seconds of your conversation. Captains hold their title loud & proud, and some may use it to their advantage because we all know- ladies love boat boys. They are smart, charming, and driven. They are so driven that they can hit the bars harder than most guys and still be up for work disgustingly early, and are pleasant enough to rack in those TripAdvisor reviews. They are overworked, generally exhausted, and barely have time to pack their lunch, so good luck getting these ones to take you out on a real date. Time with them will be spent watching Netflix, eating 420 takeout, and talking about boats, boats, and…boats. 

3. The Beach Bums

He is most likely donning a man bun, listening to Bob Marley, and carrying a mason jar full of weed in his backpack. They are laid-back, kind-hearted, and creative. These are the guys that usually have a lot of girls around because they make such good friends. The Beach Bums are obviously the best beach dates- they know the best hidden spots, they pack snacks, usually bring a hammock, and are totally stress & drama-free. 

4. Massholes 

It seems like New Englanders make up about 79% of this island. They gave up the cold, the patriots, and Dunkin Donuts to move here and sometimes they appear to be a little bitter about it. They are known for their quick wit, fiery personalities, and pride for their hometowns. Wicked smart, deeply passionate, fiercely loyal, but may have to check with their “Ma” before bringing you up north to meet the family. 

5. The Chef 

They catch the end of party crowd at the popular local bars, then head over to close down Quiet Mon, while usually still wearing their bandanas. Most seem to have girlfriends, smart girlfriends, because uh…the man can cook. They have a good sense of humor and thick skin, built up by spending hours a day in a kitchen full of men. You don’t get to know them as quickly as the front of the house, but when they are out & about, they definitely know how to blow off steam after working their asses off during high season. 

6. The Lost Boy

These are the ones with a twinkle in their eye and wings on their back. They are ready to take off at the next opportunity for adventure. 98% of them have a beard, and probably a well-kept man bun. Romantic and charming, but the whole free-spirit thing prevents them from being tied-down. Listen to their stories, they are always the ones with the good stories. They can be found on a surf board or a sailboat. Lost Boys are runners, they ran from wherever they came from and they will run again…


2 thoughts on “6 Types of Island Boys 

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s