Specifically I think if I were to date I'd be expecting or preparing for the let's just be friends talk because that's what has always happened to me. I would be bothering the person I was dating by constantly needing reassuring but I'd probably just always be prepared deep down for it to happen. I wouldn't have any fear of being cheated on or anything either.
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Self esteem issues really complicate dating however, if you never date it becomes somewhat of an endless cycle. You don't date because you don't feel you're good enough and you don't feel you're good enough because you aren't dating anyone.
I wouldn't recommending trying to jump into a relationship all out when you're vulnerable but you shouldn't be afraid to take risks either. There are ways to build your confidence without necessarily dating. Just putting yourself out there and seeing that you have worth and that you are desirable go a long way.
I was once very insecure. I still have those lingering thoughts 3.5 years into a relationship but I would have never gotten out of the rut I was in if I didn't take a risk and put myself out there to be rejected.1