When hunting for a date-night idea, there's a fine line between being appropriately thrifty and downright cheap.
Happy hour? Sure. The snacks and drinks are discounted, but it's not like you're clipping coupons. You don't have to ask for the deal.
The 2 For $25 experience at Chili's — that's a little dicier. Let's explore.
Something nice about the 2 For $25? It's available any time of the day. Other places in town have limiting factors. You can get a bottle and board for $25 at Postino — but only after 8 p.m. on Mondays and Tuesdays. Macayo's is offering a two-fer deal — but only until July 1, in honor of its 75th anniversary. Mellow Mushroom offers a Date Night package — but only if you're willing to take the food home. There are no such limits at Chili's.

Chili's provides two Happy Hour menus while requiring you to turn to your phone for their food menu.
Bri Valdivia
Other establishments also tend to limit you to an appetizer and two entrees, sometimes even less. Chili's goes whole-hog and includes a small appetizer, sizable entrees, and a dessert. That's a three-course meal for $25, which you'd be hard-pressed to find at any other sit-down establishment.
In the fast-paced world of casual dining, the pressure is always on guests to have their order ready before the server starts cycling through their oversized section again. Thus, both parties must agree on an appetizer and dessert and choose respective entrees in rather short order. If your date is easygoing, it's a breeze. If you're a bundle of people-pleasing nerves, then this setup is a nightmare. You may, for instance, replace your coleslaw with mashed potatoes and realize only too late that you now have two potato-based sides on a tray in front of you. (See photo below.) Too much potato. Humiliating.

The oft-lauded Chili's Baby Back Ribs with a generous serving of potatoes and a Bacon Ranch Quesadilla.
Bri Valdivia
Overall, the food at Chili's is plentiful, filling, and cheap. However, we must acknowledge that the $2 For $25 is not a good option for a first, second, or even fifth date. Too fraught. We do recommend it for those comfortably in a relationship looking for a last-minute meal in a spartan environment. You're paying for two entrees from a limited menu and getting a free, half-sized appetizer and dessert thrown in, bringing their price point down to an amount that honestly feels appropriate for the quality of food and atmosphere. (Drinks not included, of course.)

The Skillet Chocolate Chip Cookie. Yes, the skillet is hot, yes, you will burn your hand on it in front of your date.
Bri Valdivia
Love on a budget. Take notice, food scene.