Quantcast Gentlemanlike First Dates + What to Wear - Gentleman's Box

Gentlemanlike First Dates + What to Wear


As gentlemen, you always want to make a memorable first impression, especially on a first date! Movies are overdone and impersonal, but finding new and creative ways to spend time with your date can be tricky. Not only are we here to help you find some very gentlemanlike first dates that are sure to be memorable, but we are also going to share outfit options for each date!

Get Moving

If you find out your date likes to be active, whether it’s indoors or out, what better way to bond than over that mutual interest. If it’s a beautiful day out, find a place to go on a hike or a nature walk, or move the activity indoors and find a rock climbing facility! Have a dog? Meet up and take your pup(s) to the dog park to have a playdate. All of these activities will allow you and your date to have lots of time to talk about your interest and hobbies, find out if you’re compatible, and make a great gentlemanlike date!

Athleisure looks are very “in” right now, so this is a great way to show off your styling skills! Pair joggers, a nice fitted tee, and some bold sneakers together and you’ll not only be comfortable, but trendy! Here is some great inspiration from our Pinterest Boards!


Heatin’ Up

They say the best way to a man’s heart is through his stomach, so why not take your date to a cooking class? You get to be interactive, make something delicious, and talk in-between the Chefs’ pointers. Taking a cooking class is the best of both worlds; you get to still have dinner, but that you’ve made yourself, and then talk after + this will be a very flirtatious way to interact with your date, which is never a bad thing!

Look a more dapper on this date with a simple button down and a nice pair of chinos. You’ll have an apron on during your class, but after, you’ll want to look your best during the dinner! Here is some great inspiration for ya!


Have Some Fun

What a better way to spend a date than at a carnival! It’s getting to be that time of the year where your country fair is coming up, so buy some tickets, ride some rides, play some games, and chow down on some good deep fried food. This will be a great way for you and your date to laugh, interact, and show off by winning your date a giant teddy bear.

Since you’ll be having lots of fun, make sure your outfit portrays that! Go for a printed shirt or shorts that have fun colors. This will show you know how to have fun and not be serious all the time! Here is some fun inspiration for you!



If you want more tips and tricks on everything men’s grooming, fashion, and lifestyle, get your own Gentleman’s Box! In every Gentleman’s Box comes the Gentleman’s Post; a mini magazine with tips, tricks, and articles for the everyday gentleman! Get yours here: https://gbx.es/2JxXWKv

More posts you might like