Never spray yourself more than twice. Ever.

The problem with cologne is—or at least it seems—that some people just simply do not know how it should be worn, as evidenced by this and this, for starters. If you wear it properly, people shouldn’t really smell it unless you’re right up next to them, and even then it should be nothing but a subtle pleasantry.
The art, then, is obviously in the application. The best time to go about applying cologne is right after your shower but before you’ve put any sort of shirt on. Spray yourself no more than three or four times, in whatever areas you prefer—typically the chest and the sides of the neck, though the wrists aren’t a bad place either. This allows the cologne to mesh with your body’s natural oils to create what, essentially, becomes your own unique scent.
Cologne should never be sprayed directly onto an article of clothing, nor should it be applied liberally to your various body parts—unless of course you want to smell like the Macy’s cosmetics department. This isn’t lotion. Subtlety is key. You don’t want people to be able to smell you from across the building; what you want is to be able to be pleasant to those privileged enough to get close to you, especially that special someone who gets to get really close to you.
If you need help choosing a good cologne, check out Clinique's Happy For Men, Estee Lauder's Pleasures For Men, or L'Eau De Issey Pour Homme for a few examples of those that can leave a great impression without knocking anyone over.
Never spray yourself more than twice. Ever.
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