Do you think they'd take turns doing things they think the other would enjoy? That's what I think.

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They double date a lot with Trixie and Glim Glam.

Or just Glim Glam when Trixie is out on the road.

Basically, lots of Glim Glam.

I'd say that, at the start, Twilight would try and be formal, going on stereotypical "Dates", while Dash would be far more laid back.

Twilight would go for restaurants, movies, park settings, and the occasional "reading date", while Dash would be more interested in things they'd both enjoy, as well as some things like trips to flight shows, and VIP seating to wonderbolts events. I'd imagine that they'd get more relaxed and comfortable as things went on, and Twilight would eventually get relaxed enough to just go for hanging out with romantic intent, but, for a while there, Twilight would definitely be the textbook definition of "Proper dates".

...

Now, If you'll excuse me, the question gave me an idea.

Maybe a picnic in the meadow,Watch a Daring Do movie,or maybe Twilight in Rainbow Dash picked the Date separately

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A lot of stories in the group have depicted the get together from either pony's initiative. Overall, a lot of the consensus has typically been that Twilight is the less experienced of the two and turns to books/Rarity on dating advice, which tends to lead towards more traditional romantic settings.

As we're in Season 8, and we've seen both characters grow a lot, I think the two are already very comfortable together. Rainbow Dash likes danger and excitement and adventure, and Twilight has proven not to be the introverted bookworm that forgets to come out of her room for weeks on end to perform basic living tasks like eating and so on. Those sorts of stories always felt silly and shallow anyway.

I think it really depends on what it is you're wanting the pair to do. Following canon, Twilight is far more chill than she used to be, and wouldn't insist on a big elaborate courting ritual. She knows Rainbow Dash isn't interested in that, and she knows that Rarity is hardly the best source of advice. Instead, she'd offer to go flying with Rainbow to somewhere with some natural beauty and away from others. They can both travel pretty far in short order flying.

They could also just hang out and share a meal. Twilight is pretty keen on hayburgers and fast food, which probably is right up Rainbow's alley.

Dash seems to enjoy music and sports. Both of which lend to date possibilities that are more planned and goal-oriented. I think she'd see the appeal to that for Twilight. Rather than just go to some random sporting event, she'd bring it up and get Twilight interested. Twilight would read up on the history and so on for the game, and enjoy herself a lot once there to witness. This instead of trying to surprise Twilight with something only for it to fall flat.

Overall, I think it is less about what exactly they do, but more about how they'd approach doing it. They both have a fairly wide range of interests, and both seem to know each other pretty well at this point and have ideas on how best to bring up date ideas to each other. There is enough overlap in their interests that I don't feel like they'd have to spend much time taking turns being bored while the other does what she wants.

I can see Dash taking twilight to secret, beautiful places she's found while flying, just to show her how special she is Or twilight taking Dash stargazing

They'd snuggle up on the couch reading daring do books

Flying together and snuggling in a cloud.