Have been trying to date over the past few years and after a very very large number of rejections I bit the bullet and asked a couple of my friends what they thought was going on. To my surprise, all of the women said that I have "niche looks" meaning they thought that while I'm not "ugly", I'm not traditionally attractive for a guy. They don't think I'm the equivalent of Steve Buscemi or anything along those lines, but I'm no George Clooney or Patrick Dempsey either. This kind of makes sense because of my dating history in that over the past few years I've dated dozens of women with varying amounts of success. Some only wanted the first date, some lasted for 6 months, but that is the extent of it.
To provide a bit more context, I'm 5ft6in tall, very muscular and fit. My celebrity lookalike is Curtis Mayfield, but I cannot sing like him unfortunately

. I own a condo in DC and I work as a partner at a boutique law firm in a finance practice. I have a fair amount of hobbies (obviously weightlifting/exercising, BMX bike riding, collecting tattoos, perfecting my beef wellington) and a solid friend list, and I have never heard from anyone that I'm "boring" but I'm not putting it past there being some sort of social defect as well that is preventing me from making a solid connection with someone. I provide that info not to brag or point out that I'm a catch but to establish that I have my life in order as a baseline. The women that I have dated have never brought up my "niche looks" but usually would tell me they just weren't feeling it and I did not want to pry or try to force them to come up with a "reason" for not wanting to continue to see me.
Do folks have any thoughts here, absent plastic surgery, that I could use to improve my dating life in this regard? Do I need a matchmaker? The vast majority of women that I've dated have come from online dating as I'm not one to approach in person IRL other than two one-offs over the years.