First of all, you deserve what you think you deserve. If you think you deserve to be with someone you want to be with, then that's what you deserve. In other words, no one can tell you what you deserve.

Second, what you are experiencing in having difficulty knowing how to approach someone is common. I know that doesn't fix anything, but a lot of people have the same difficulty. I've been married for thirty years and I find it really easy to start up a conversation with just about anybody.

If you notice someone coming to the end of a workout on a machine, you could always say "the last 5 minutes are the hardest aren't they?" Then just keep walking away. That way you can't be rejected. Now you've practised speaking to someone. If you see them again it might be easier to talk to them. I think most people, especially women, don't like the confrontational aspect of someone talking to them. They don't want to have to reject someone, although some women don't care about blowing someone off.

If you speak to someone and then walk away, there's no threat, but there is the potential to speak to them if you see them again down the road. It also opens the door up for them to speak to you.

Just make sure you say something appropriate for the walking away part, like:

Doesn't it feel great when you get to the end of the workout?
That machine can be temperamental.
You seem really determined.

Anyway, you get the idea. Be genuine with your comment, but keep walking away. If she's interested (and available), you've opened the door for her to talk to you, without the worry of instant rejection.

Nobody has to settle.