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A Guy’s Guide To First Date Ideas And What To Wear

One of the most nerve-wracking things a guy has to go through is the first date; a right of passage, so to speak. So many questions running through your head, we bet. Where to go? What to do? What to wear? Relax, here are five tried-and-tested first date ideas that are light and fun to do. We’ve thrown in some outfit ideas, too.

Date Idea #1: Saturday Hangout

Pro Tip: Plan an afternoon of pleasant roaming around. Think art galleries, weekend markets, museums, bookstores, and an excellent merienda.

What to Wear: Wear something comfortable enough for long walks, like sneakers, jogger pants, and a collared shirt.

Date 1

A printed button down, chinos, and loafers spell w-e-e-k-e-n-d.

Date 2

Date Idea #2: After Work Drinks

Pro Tip: Choose a place that’s not too loud so you can still enjoy some conversation.

What to Wear: You can’t go wrong with blacks, grays, and deep blues.

Date 4

A blazer keeps the look dapper and polished.

Date 5

Date Idea #3 Chill Movie Night

Pro Tip: Make sure you’ve arranged for movie tickets and dinner reservations (nothing fancy – yet) beforehand. Plan a fun and light post-movie activity, too. Coffee sounds excellent.

What to Wear: Pair your usual jeans and plaid shirt combo with a cardigan or bomber jacket.

Date 7

Date Idea #4 Brunch

Pro Tip: Like in movie nights, take care of the reservations for brunch.

What to Wear: Don’t look sloppy, but don’t overdress either.

Date 3

Date #5: Run Sesh

Pro Tip: Assuming you and your date are sporty, running dates are fun because you already have a common interest. Schedule your meet-up early in the morning or late afternoon when the weather’s pleasant. Stay hydrated and bring a change of clothes because you  know, you two might be in the mood for a recovery meal after.

What to Wear: Sportswear that fits well (no awkward bulges and loose elastic bands, please). Conscious of sweat marks? Stick to blacks and whites.

Date 6


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