lol. I smoke socially, generally one to two cigars or cigarillos on the weekends....or less, like I said, depends if I'm "out and about"....I'm not one to "light up" at work, just for the [censored] of it.
Anyways, if you can find one, a Don Diego Cigar would be a good first time to try.
Best to light the cigar with a butane lighter, vs, a classic "BIC".....otherwise you'll get a strange taste of the lighter fluid as it's pulled through the cigar....
I've found most traditional "cigars" to be very bland. But as mentioned, the Don Diego I had was about the best. Never had a Cuban though
Start with something "mild" like a cigarillo, be it a White Owl, Swisher Sweet, or a Black and Mild.
And remember, you aren't inhaling the smoke...lol, you'll kill yourself

especially if you've never smoked.....you just sort of "taste" it in your mouth then expel it
And they aren't meant to be "chain smoked" lol...the longer they burn, the hotter they get, or so it seems anyways