>>2 3 has so many really good main characters. I've fallen in love with much of the plot as well, even with how depressing it can be. Playing Persona 3 feels like watching a tragedy - it can often be bittersweet, but it's so good. Playing Persona 4, to me, feels like coming home - just seeing the Dojima family + Adachi puts a smile on my face every time. Persona 5 is a bit of an escapist ride for me, but I don't mind it at all - a bunch of the characters /are/ really fun, and I love thinking about the many changes Royal will bring.
Lastly, if you didn't know prior - there is one game in the Persona series where you can romance a guy, Persona 2: Innocent Sin. It's available on PSP but can be emulated pretty easily too. I'd recommend watching an LP of it instead, though - the gameplay absolutely has not aged well at all.