I experience this as well. I didn't cry for years between middle school and when my friend died unexpectedly at age 21, so about seven years. I've cried twice between 21 and 25 and a half, which is where I am now. This was despite feeling lonely, regretful, suicidal, hateful, frustrated, and everything else in spurts throughout that time. I often wished for the ability to cry and frequently passed what I would consider the emotional threshold... it just wouldn't happen for me. I have been at the point where I had the rope around my neck and was seriously contemplating just doing the deed, yet no crying was involved at all.
For me it's not anti depressant related because I didn't start those until maybe six months ago. If anything my bupropion has made it easier for me to cry as I teared up at something quarantine related a few weeks ago and was shocked.
For me I do think gender roles are part of it. I remember being concerned with seeming tough when I was younger, and the other boys definitely would've made fun of me. When people cried in school, it was always an embarrassing freak out moment for them that made everyone else feel uncomfortable. I also think I associated crying with my mom getting mad, because she'd always start crying and yell and isolate herself and slam doors if there was conflict. My dad would certainly never cry. Maybe I didn't have a healthy model of when and how to cry, so I never learned? I also think I tend to avoid or suppress painful emotions when possible, so maybe that has something to do with it.