This is something I seem to face lately as a 30 year old guy. I've never been good at dating. It's not something that has ever come naturally to me and I've always struggled to not be shy when it comes to meeting people and putting myself out there. To be fair, I have had one relationship before (so I know it's not hopeless), but it's not easy (for me, at least).
I'm very lucky in the sense that I think of myself as being attractive (at least to a point of not having anything about myself I dislike or would ever want to change), I am extremely tall, decently fit, good job, educated etc. On paper, those qualities are supposedly good assets to have, but they don't translate to success for me. On the other hand, friends of mine who have far less going for them date like it's no big deal.
The most frustrating part for me is that I really don't feel like being shy is equal to being antisocial (which is the #1 thing I hear whenever I bring up being shy). I'm actually a very social person and work in a role that requires me to build relationships and connect with others. My shyness has nothing to do with that. My shyness comes from a place of not wanting to bother other people, make them feel uncomfortable in any capacity, or intrude on their space. This is why when I meet someone I like, I always hold back because the last thing I would ever want to do is make anyone feel uncomfortable. I guess my friends are the opposite in that sense.
So I feel like being shy shouldn't be the end of the world. It's something to work on, obviously. But a lot of us who are shy just don't want other people to feel uncomfortable.