I was just wondering if mentioning the clothes issue and how it kind of bothers me when he weard something really old looking on a date means that I'm trying to change him. And I think high socks with shorts just looks bad (it was winter when we first started dating lol so this didn't happen)
I don't need him to dress up but think he would look even better than he already does in clothes that fit better
Most Helpful Guy
A lot depends on the tone, and how you deliver the message.
If it comes across as very negative, he could get defensive and lash out.
Guys don't like unsolicited advice. It comes across as nagging. As basically saying "I need to tell you this, because you're too stupid to figure this out on your own."
That isn't what a girl means, I know. But that's how it comes across. Unsolicited advice is never welcome.
If you can find a more appropriate way to ask him, you'd stand a better chance of getting his cooperation.