So how do I tell him to dress better. Last weekend I told him "hey, you've never seen me with the same dress or outfit twice". He asked me once to wear a maxi dress next time we saw each other....I did. But damn, I dont know what to tell him.
Offer to go shopping together is my favorite - much the same of "Hey lets workout together", but thats mainly because I love the input of the person I'm dating.
A more direct approach might not hurt but feel it out.
You do realize that you're trying to change him, right? How often does that work again? It's pretty clear that you aren't doing this out of the kindness in your heart so just beware that you're breaking a golden rule here.
This is why I say to feel it out.
Of course, my experience differs, and with this particular subject namely : One of my best friends is clueless when it comes to fashion. Hes a great guy - sings in a band, athletic on a team, very personable - but just clueless when it comes to fashion. He'd like to change, and I've done what I can - as have our friends - and is open to input, but we can't tell him to not wear swim trunks every day.
I also don't know the context of this particular situation. Honestly I'm okay with changing little things I don't care about to please the one I'm with, especially when its bettering myself like eating healthier or wearing nicer clothing.
I'm only 19 so usually we just start being together but this is the first time I'm gonna have to get to know another person over a date. Any tips?
Listen. Dress nice. Listen. Do something fun, don't see a movie. Talk. Listen.
It seems silly to say, but just be yourself. Don't be afraid to Google for silly first date questions to ask during silences : You're trying to get to know each other, the crazier the better.