I have my 5 year college reunion coming up this september, should i go on roids for the summer so I can put on 10-15 pounds of muscle and roll up there 6 foot 185 with abs. I think that would be pretty solid. I'd also rent/borrow a nice ass ride etc.
Do NOT go the 'nice ride' route.
Five years out, you're not expected to have done shit with your life, so if you try to front, you're only going to look like a chump.
If your girlfriend is fat, however, do not take her. You should definitely take a hot date, even if you're flat broke busted.