If you like cigars that aren't super heavy, Punch cigars are good (particularly the London Club), I haven't gone wrong with "Punch" cigars yet, and they are not expensive either:
Never used this website, before, but this is the cigar I'm talking about:
http://www.famous - smoke.com/punch+london+club+cigars/item+9729 (that website asked me to remove that link for some obscure reason, -chadz)
Also give up on the chew/dip man, it's disgusting and a bad habit to get into (I chewed all through high school and as a young adult) . Some women can deal with the smell of smoke on a guy, but not many are going to want to be around you when you're chewing.
When I was smoking "cigars" daily, I would just smoke a Black & Mild Wood tip cigar (not the wine flavored wood tip):
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