LAB, the issue isn’t as black and white as you’re making it out to be. “Asking out” can mean anything from asking for his/her number to go on a date, which I think is inappropriate, to asking for his/her Rebbetzin’s contact information so he can find out more about her, which I think is fine. I neither support nor oppose asking out in either situation.
Hashem has His ways of getting people together who are meant for each other.
Provided both parties follow the spirit and practice of halacha, there is no reason this can’t work out.
Is this different than someone marrying their friends’ sibling, which happens pretty frequently? This just requires more carefulness and tznius to ensure the initial impression holds up.