While Earring(s) on a man or lack thereof could never be a dealbreaker, my best advice would be to pierce both ears simultaneously. After the healing time - you can then wear an earring in only one ear (or a pair) if that is still what you prefer.
MeetVast raises an opinion about face and hair. This is how I like them most. I like how earrings can blend with other "fashion jewelry" &/or or clothing to create a larger image of magnificence. If you wear eyeglasses - let your earrings match their shape and also that of your hairstyle and face--and also that of your outfits. Earrings simply will not make you feminine--nor will any style of pantsuit to match the style of accentuation; and, I like earrings to accentuate physical features.
These are styles long before my time but I love for earrings to magnify the entire appearance--while blending into it. I am also open minded.
https://i.pinimg.com/originals/77/ee/2a/77ee2ac3117cb1ae1cc9441138e8d45b.jpg
