Is it pointless for me to approach women that are older than me? I (25M) tend to feel like I would feel comfortable dating someone as old as 30, and I’ve had some good, in-depth conversations with women around 27-28, but I don’t know if this is really worth my time (or, to be more technical, worth their time).

On some level I have to wonder if the likelihood of their having more schooling or a better job near-instantly makes me unappealing, plus question if that difference in life experiences is reason enough to not attempt it. On top of which, I feel, is a slight stigma towards a man dating an even slightly older woman.