It seems to me the issue here is that you are more worried what everyone, ie your friends, else is going to say about you when they find out you went to the prom.
At some point, you just have to not worry about it anymore. If you start dating a fat ugly woman because you like her who gives a crap if your friends give you grief.
Just let it slide off your back and they will quit.
I will say this, if my daughter was 18 and I found out she was dating a 27 year old, I don't know what I would do. That would be a tough pill to swallow. It's hard for me to imagine an 18 year old having the maturity of a grown man. Not trying to be an *** but it seems to me like the 27 year old man had some issues more so than the girl.
Also to respond to someone else paying bills and living on your own don't neccessarily make you mature. I've seen 40 year old guys that were less mature than a 20 year old girl. I think everyone is different, it's just hard to imagine an 18 year being there that's why people have an issue with it.
Last thing I have to say is that to me if you decide to go out with a younger girl you should know that she is going to want to do things that girls that age do usually. It doesn't matter if your 50, to me you should go. If she's good enough to go out with and everything else is worth it she should be good enough to take some ribbing for and to feel uncomfortable for.
Last thing I gotta say is you could be asking for trouble. Without knowing you and knowing where you are in your life you could get to the point where she starts wanting to experience all the things you already have and you may have passed that point and it could happen again and again. The prom is first. Then what about when she turns 21 and wants to go out every night. And on & on. This happened to a guy I know and now he never wants to do the things she wants to do becaause he is tired of that scene. She on the othere hand is just getting into it and they get pissed at each other all the time.
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