Bill: 1 time. The only time was because Bev was drunk and she kissed him.
Richie: 90 times. You guys have the definition of an on again off again relationship.
Stan: 2 times. Once because he felt guilty he wasn't dating a Jewish girl. The second time you got in a fight.
Eddie: 1 time. His mom.
Mike: 1 time. He felt bed you kept on getting bullied by Bowers for dating him.
Bev: 7 times. The first time because her dad found out and the rest of the time because you guys fight a lot.
Note: Sorry it's getting SUPER repetitive I'll try harder next time 🙂