So let's say you actually get to Equestria? Which pony look for and try to ask out? For me I know Chrysalis would be out of the question so I'd go after Rainbow, Moondancer, or Bon Bon.
Badly worded prompt but I'll have some fun with it anyways.
>Attempt to find Ponyville
>Do my best to ensure that I am a rational and reasonable person
>Use previous knowledge to better my chances at building friendships with the Mane 6 and others.
>Take up work to slowly own a home.
>After taking a long time to get that done, attend a motivational event.
>Speak to Iron Will about helping me to work up the nerve to ask out someone I care for.
>Work as hard as I can to better myself and show I'm serious about it.
>Finally, when the time is right and I'm confident in my chances, I work up the to ask out