First of all, I think Jeff is right. My first thought was to not respond unless you are asked a question. But, if you're inclined to go since Rob thinks you should...
Yes, you do need a new shirt. I don't care if you have ones you already like. The point is to shake things up and do something different. Do you have a Robert Graham? They're pricey but gorgeous. If you can splurge, that's what I'd recommend. And if you are near a Nordstrom Rack you can usually find one or two there for about $80 (reg. price is $200+). Use this opportunity to try on a new look. And shoes too! I love it when a man is wearing great shoes.
No, this is not W-oriented. Pick out a new, different cologne. Get the scent you like.
Did you always let/make W make the plans? Not sure I'd pick the location since that means you're doing the work for her. But if it's a good 180, then ok.
Definitely take separate cars. Stick to small talk. Talk about yourself. This is where it would be good if you had a new hobby to discuss. But general small talk will work. What do you discuss with coworkers (besides work)? Or other acquaintances?
If you love somebody, set them free. http://tinyurl.com/2empx2g
