[fistofjohnwayne]

"Q: What do you call a man who dresses well? A: Grown-up."

As for the advertising, I think a well-dressed young(ish? -- the assumption being younger, single people are more likely to use Grouper) person engaging with potential customers in casual conversation at the popular coffee shops and lunch hangouts in your area would go a good deal further than schlepping to work in the same shirt each day. However, I haven't lived in New York and perhaps the people there are less open to casual conversation.