Dating is hard. There's the pressure of what to do, what to wear, how to be yourself (but cooler). You know the drill. Luckily, we can help with a few of those things — mainly, what to do and what to wear, because those two things go hand in hand. After all, you don't wear a suit to a picnic. Or maybe you do. We won't judge.
That said, here's a list of fun date options, and suggested attire for each. After that, you're on your own.
Date One: A casual dinner at Oddfellows
The relaxing Oak Cliff restaurant has a menu filled with burgers, grilled chicken, and a little bit of comfort food (buffalo mac and cheese forever). There are plenty of cocktails and beer on tap to loosen you up a little.
What to wear: For ladies, Riffraff Dallas has a vast selection of casual tops and jeans from which to choose. As an added bonus, it's not very expensive, so you also won't be wasting money on a new outfit for a date that's a dud. For guys, don't assume that Bishop Arts means you can slack on style. Go with a nice button-down and a pair of fitted jeans from your stylist at Trunk Club Dallas. Like your outfit, this date should be laid-back and easygoing.
Date Two: A day at Klyde Warren Park
Now that the ice is broken, a day (or evening) at Klyde Warren Park is the perfect way to get know one another better. Dallas' charming park has outdoor concerts on Thursdays, games, and a plethora of food trucks, so don't worry about bringing a picnic basket.
What to wear: You need an outfit to match this fun and light-hearted date, but here's a tip: Don't wear white. Grass stains aren't a good look. Ladies, you can't go wrong with a sundress or romper from the eclectic Gypsy Wagon, and for men, a linen shirt with a pair of Stanton shorts from J. Crew are always a plus.
Date Three: Drinks at Soda Bar
With incredible views of downtown Dallas, the Soda Bar at NYLO South Side is the ultimate bar for after-work drinks.
What to wear: For this date, you both want to wear something that will easily transition from work to play. Ted Baker London is a one-stop shop for this, and the one and only store location in Texas happens to be at NorthPark Center. The British brand is known for its contemporary day-to-night apparel for both men and women, so you'll be showing your style stripes with this outfit. More than likely work was stressful, so sit back, sip a cocktail, and know you look good.
Date Four: Brunch at TNT Tacos and Tequila
It's date four, and hopefully, by now you're showing the real you. This also means it's about time for a brunch date, where you can stuff yourself silly. Consume all the Belgian waffles, street tacos, and agua frescas your stomach can handle for just $22 at this casual restaurant in the Quadrangle.
What to Wear: Since it's all you can eat, we suggest something comfy; a classic street-wear look is ideal. Possibly a cheeky T-shirt and a pair of joggers from H&M at NorthPark Center. Ladies, a maxi skirt with a drapey tank from Splendid or Free People (also conveniently at NorthPark Center), would be perfect. To avoid the after-brunch food coma, walk off the waffles and explore the city together.
Date Five: Romantic dinner at Madrina
Pat yourself on the back, because you've made it to date number five. This French-Mexican fusion eatery pulls out all the stops in the kitchen, and so should you with your wardrobe.
What to Wear: Take the opportunity to really impress each another with a well-tailored suit from Suitsupply for him, or a chic little dress for her from Tootsies in the Plaza at Preston Center.
Dress to impress on your next date.
Hiatus will open at Town Hall Square in September 2026.Photo courtesy of Hiatus