Alright…kiiiiind of a problem here…well actually I just want to see if ya’ll are paying attention because reeeeaaasons. So here it is, a love square, wanting to see if which pairing you think looks better(just an opinion), I have some reasons for each one. Also changing my Oc’s name from Willbert to just plain Will.

Rarity x Will- Been in business for a long time, Will travels around Equestria selling Gems and such with pretty good prices. And Rarity is Will’s number one customer, always buy almost all of his Gems and giving the most intriguing conversations. I suppose if they got together Will could find Gems for Rarity while uses the resources that she has on her. Both can be fancy considering they both are French(yes Will is French). But then there are those times when Will has to leave to make some bits from his other customers, but then Rarity might feel alone and it might go not go well in the future…you know the wife will start worrying and become either depressed or lonely and…yeah.

AppleJack x Will- I suppose AJ will enjoy Will’s personality and enjoyment of helping the Apple Farm, yes he does help AJ when Rarity is unavailable. So I guess they’ll be happy and not have any problems considering they could have the Twilette relationship but a little less hate. But then there is the part when Will has to forget about his current job and officially stay with the Apples, but Will likes to travel so I’m not exactly sure how that problem is gonna solve itself.

Rainbow Dash x Will- These two are more of the “opposites attract” type which I can see that, Dash being the athletic stubborn Rolemodel while Will is the cunning responsible Merchant, these two are so different yet so similar. And both don’t have to change each other/themselves for the other, Will can still travel around Equestria and Rainbow Dash can try to be a Wonderbolt or whatever she wants to do with her life. And they don’t have to feel alone because Dash can easily use her speed to fly around Equestria and easily find Will on his travels and give him a big ol surprise hug. Not sure if they’ll have any problems though, kind of a mystery.

Will(kinda old) -> https://www.deviantart.com/didun850/art/Mlp-Oc-s-2-558424425

Note there is a right answer lol…

MlpFim/Rarity/AJ/Rainbow Dash (c) Hasbro and
Will/AfterVerse/Art (c) (me)