Mark
You two had been very flirty with eachother til Tyler got annoyed and said "just ask them out already" then Mark said "how about it (Y/N)"

Jack
He asked you to a highschool dance in junior year

Ethan
He awkwardly admitted that he likes you and asked you out on a date while blushing and stumbling on his words, he thinks its embarrassing but you think its adorable

Dan
He texted you while you were both sitting around in his flat

Phil
He invited you to hang out with him and then you asked if it was a date, je asked if you wanted it to be and you said yes