Who was more the ladies man?
Kirk was World Heavy Weight Champion in this department as well.
Riker ( not so much … “sad trombone” sound in comparison ).
OB
Problem with Riker is that he didn’t know how to treat a woman when she starts actually all hysterical and such.
Kirk knew, that you need to grab her by both shoulders and shake her.
Ironically, the the same move is use when Kirk kisses a girl. Grab her shoulders and pull her toward you.
Long experience taught Kirk that kissing a girl would make her hysterical. The signature grab-and-shake was to dispel any hysterics before they could start.
I have to give my vote to Kirk. Riker had, what, 5-6 girls in 7 seasons? Kirk had a different girl in every EPISODE.