Dating anxiety

I'm 24 years old and have never dated before in any capacity. I'm very shy and struggle with anxiety, but I have tried flirting with guys before. The problem I keep running into is that every time I think I've found a guy who's genuinely interested in me and who I have ongoing conversations/flirtations with, it always ends up that he's been leading me on. Usually I just end up assuming that I misinterpreted things and he wasn't actually flirting, but the last time this happened a couple of my friends had specifically commented on the fact that the guy seemed very interested in me, and then barely a month later I found out he was in a serious relationship with someone else.

The fact that I've been led on so consistently and already struggle with anxiety means that I now find it difficult to trust guys enough to even flirt with them. This is only made worse by the fact that my anxiety about inexperience is only getting progressively worse as time goes on. How do I trust that guys aren't going to continue playing with my feelings? And how do I trust that I'm not going to be rejected for my inexperience?

its the same issue with me. its gotten to the point I don't even try and date for when I do, i'm usually the one doing the work. its all in matter of what you gut is telling you. there are obvious signs however. remember this, a lot of guys go after sensitivity and shyness. makes for easy conquests

You would be surprised. From what I gather on the internet for some men it's not a deal breaker. Some guys see it as a great opportunity because you have no romantic past tied to you.

Easiest way to avoid being led on is just to ask outright.
Just ask if they had a nice weekend with their significant other. If they look confused and say they aren't seeing anyone, you just apologize and say you must have misunderstood.

I think therein lies the problem. The op already admitted to anxiety and shyness and kind of makes the straight forward approach, though not impossible, quite difficult.

Flirting with people is such a difficult thing to understand. I know because I've mistaken interest from ladies more than enough times to know that there are enough people out there that don't intentionally flirt to show interest but just tend to do it. I know that doesn't make it any easier on you but as for the trust issue, thing to understand is just because someone flirts, if it's in their nature they may not be intentionally "leading you on". Why I say that is that it affects how you view men in general. Men (and women) can flirt and not necessarily want anything more than that bit of fun. I don't understand it myself, because I don't do that but I do know from experience it's more common than many want to admit. So don't write them off as being bad guys that lead women on (and I'm not singling out men over women in this, this goes to men that have the same issue), it's their playful nature. Unless they actually make a move it's not necessarily to gain anything with you. they may just like the attention they receive from it.

I think your anxiety issues and getting over them may be the key to finding the guys that are "for real". You'll have to learn to be forward and make the difficult moves to find out their true motives but with the anxiety that makes it hard to do so.

As for inexperience, I doubt many men would write you off for that reason and I don't know many.. no, any men that actually ask any questions to find that out when trying to court a female.

I'm sorry this happened to you; however, if I were you, I'd keep trying. They can't all be in a relationship, right? So if you keep looking you might find someone who is available. I know it's hard to trust and that it' frustrating, but don't give up.