Getting older I can only say: looks are overrated. During my time I used to have all kinds of hair styles: metalhead with long hair, medium length, short hair, almost no hair, and right now I have like half a centimeter, because it's so hot weather and I sweat a lot and felt uncomfortable. Last time I cared about "how do girls look at my hair" was probably in my teens but even then I went against the stream, because metalhead long hair was far from being desirable.

IMO you should focus less on how do other perceive you (your look) and more on how you feel yourself. Having less (no) hair has so many benefits I can't even think of going back to anything longer than ~inch. Sure I might look dumb, but that feeling of air breeze on my skull is so refreshing I couldn't care less. Another benefit is much easier care. When I had long hair it felt like a chore to use shampoo, conditioner and brush the hair while it felt almost instantly "in need" of the procedure again. Now? Tsssch, I use whatever: shampoo, regular soap or just water, fast rinse and hair are almost immediately fresh feeling and also dry (huge plus imo).

And the most important note. If you ever find/found a partner who is/was with you just because your fabulous hair, I can assure you it is/was not the right one.