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I really think it's a personal thing. Myself I am uncomfortable with a guy more than two years younger than me. That's just my thing. I know several women who have great relationships and their men are 8 to 12 years younger. In this day and age I don't think people will laugh at you and if they do it's either jealousy or immaturity. At the end of the day it comes down to your own comfort zone. My observation is if you are worried about outward appearance (which it seems you are) that you need to ask what others think then you are not ready for that. You will constantly be thinking about what others think rather than enjoying and embracing your relationship. But that's just my thought. Good luck.
Ask in a way that allows him to say no without goofing up your friendship..."would you ever want to go out for coffee or something?" is much easier to manage in fun manner than "would you go to x on Saturday at 7pm". Then he can do the further asking out if he's interested.
I really think it's a personal thing. Myself I am uncomfortable with a guy more than two years younger than me. That's just my thing. I know several women who have great relationships and their men are 8 to 12 years younger. In this day and age I don't think people will laugh at you and if they do it's either jealousy or immaturity. At the end of the day it comes down to your own comfort zone. My observation is if you are worried about outward appearance (which it seems you are) that you need to ask what others think then you are not ready for that. You will constantly be thinking about what others think rather than enjoying and embracing your relationship. But that's just my thought. Good luck.
I think the age gap gets to be less as you get older. If someone is late 40's and dating someone late 30's I don't think it raises too many eyebrows. 29 and 19, that's another story, IMHO.
I tend to like younger guys (like 3-6 years younger) but I always feel like they aren't interested in me for anything serious.
This is the only reasonable response in this thread.
As an actual young guy (probably the only one responding to this thread), I'd be okay with messing around with an older woman, providing that it's at my convenience. I would not consider an older woman for a long-term relationship.
**The exception to this is if the woman were truly exceptional (I've met only one in my life that I would make this exception for). Then, I would consider it (but only if I decided not to have children). But either way, marriage would be out of the question with an older woman.
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) and I know a lot of men think the same. 
