Funny story, I tried like three shipping websites and this is what came up. So enjoy this Applejlim (Applejack and Flim) requested by frozane2001. This was one of the dates in italics so I'm doing this first. But don't worry, we still have....

Cheese and Pinkie date requested by Emochick87654321, RDApplejackRarity, MLP333, pinky_party_pony, mylittleponybooks, and frozen_drawings14

Applejack and Rainbow Dash requested by takemetothepickle, and AppleDashForever

Twilight and Rainbow Dash: requested by alepower

Soarin and Rainbow Dash: requested by RDApplejackRarity, TaraD_101, MLP333, and ohmyglob123

Pinkie Pie and Rainbow Dash: requested by PinkieDashIsAwesome, thepinkpartypony, and spotop14

Fluttershy and Rainbow Dash requested by pokemon626 (Rainbow Dash has to go on 5 dates!! OMG)

Girls Night Out requested by rekiyahblanton and freddydabear

Twilight and Flash requested by CrystalGirl17, MLP-Fluttershy, and RDApplejackRarity

Fluttershy and Discord requested by EmoChick87654321, marelineVQ1354, and horrorfan76

Twilight and Fluttershy requested by Steelstallion89

Scootaloo and Sweetie Belle requested by snowzqueen

Fluttershy and Big Mac requested by MLP333

Discord and Celestia da_nerds, and Skipper-the-Dall

Sweetie Belle and Button Mash requested by RDApplejackRarity, DerpeDarp, DerpyDaze, The_Poffy_Fluffe_ applejacks01, and JaedynGirl02

Pinkie Pie and a cupcake requested by SunSummoner13 (OTP)

Derpy and Doctor Hooves requested by freddydabear

Diamond Tiara and Silverspoon requested by Starburst758

Diamond Tiara and Snails requested by DerpyDaze and DerpeDarp

Vinyl and Octavia requested by HarplessRuby

Applebloom and Pipsqueak requested by Poisondiva4

WoW!! That is alot to cover *faints* But let's get started with this insanely awkward date.

Rarity: Applejack! It can't be that bad *fixes Applejack's dress*

Applejack: Rarity, it's a date with Flim. It can't get any worse.

Rarity: Ok I'm just trying to make you feel better. The least you could do is appreciate it.

Applejack: I'm sorry Rarity, I'm just stressed. Big Mac, Granny Smith and even Applebloom are mad at me.

Rarity: Well they shouldn't be. This whole thing is just some silly dare.

*silence*

Applejack:.... Did you and Spike have fun?

Rarity: Excuse me?

Applejack: You know, on your date.

Rarity: Well it was something!

*doorbell rings*

Rarity: Ok Applejack, good luck!!

Applejack: *opens door* Oh, hiya Flim.

Flim: Good evening Miss Apple! Are you ready? *extends hoof*

Applejack: I think so, but lemme talk to my friend for a second *motions Rarity into the kitchen*

Rarity: Applejack! You can't just keep a stallion waiting!

Applejack: I know, but I'm nervous

Rarity: For pony sake Applejack, this is Flim we are talking about here. He is atleast 10 years older than you, and the date will last no more than three hours!

Applejack: I guess you're right *walks out of the kitchen* All right Flim, I'm ready.

Flim: Great! *extends hoof*

Applejack: *places hoof on top of Flim's and starts walking* So where exactly are we going?

Flim: Well I haven't really though about it. Where would you like to go?

Applejack: How about Applebee's?

Flim: Very well *both walk to Applebee's*

Waiter: Hello! My my is Flower Buzzer, and I'll be your waitress this evening. Luckily for you this is our happy hour, so both of your meals are 25% percent off. If you have an Applebee's membership card you can get your meals for 50% percent off. Our special this week is the new Sunflower Salad, I guarantee you it is worth a try.

Applejack and Flim: *try to get a word in*

Waiter: Sorry, I get paid extra to say that so... can I get this lovely couple something to drink?

Applejack: Uhh...

Flim: We are not dating, this is a dare.

Waiter: So this is what the kids do these days. When I was you're age, ponies got dared to lick the other pony's hoof or something like that. *awkward laugh*

Flim: Anyways... Miss. Apple, can I buy you a drink?

Applejack: I'll just go with some water.

Flim: And I'll take a large cider. Thank you very much!

Waiter: *leaves*

Applejack: You don't have to keep calling me Miss. Apple. Applejack's fine.

Flim: If you insist...

*awkward silence*

Applejack: Um... how's the cider business going?

Flim: To be honest, not very well. I mean I've tried all over. Manehattan, Phillydelphia, everywhere! Flam tried to get us to Cloudsdale... but that didn't work.

Applejack: I can imagine.

Waiter: Here are your drinks. What can I get you to eat?

Flim: Can I have that salad you were talking about earlier?

Waiter: No problem. How about Applejack?

Applejack: I'll take a.... wait, how did you know my name was Applejack?

Waiter: Well you only saved Equestria like 9 billion times!

Applejack: *blushes*

Flim: What do you want Miss. Apple?

Applejack: uh can I take a hayburger?

Flim: Really Applejack? I thought you were going to get something a little more.... light?

Applejack: *mad* *grabs her water and spills on Flim's suit* *walks out the door*

Waiter: She's a feisty one!.... I like it!"

Applejack: *runs home*

Rarity: Applejack! Why are you back so early?

Applejack: *plops next to Rarity* It was a disaster!

Rarity: *pets AJ's mane* Tell me exactly what happened!

Applejack: Well, I ordered a hayburger, then Flim insulted my eating habits-

Rarity: And then what happened?

Applejack: Then I... I poured water all over his suit! Look, I know what you are going to say, but--

Rarity: Applejack! He deserved much more than some water!

Applejack: I know but,.... wait... you think he deserved more? That's so unlike you!

Rarity: He insulted the way you ate darling! That is not being a gentlecolt.

Applejack: I know *play's with Rarity's mare*

Rarity: Do you want to watch a movie?

Applejack: I don't know...

Rarity: I have 5 tubs of ice cream in the refrigerator.

Applejack: That's exactly what I needed to hear.

Pinkie Pie: PLEASE ASK

And... that's my Flimjack date.. This was insanely hard to write considering they only interacted twice, so I just ended it early. But yea, PLEASE ASK!! Next I'll probably to Twilight and Flash but we'll see...