All the time.
About half the conversations I have with my dad are good-spirited political debates. My brother and some apolitical friends often ask me for explanations of things (e.g., "What does the debt ceiling mean?" or, "Why does the news care so much about Iowa?"). My extended family on my dad's side is extremely political and highly opinionated, with greatly varying ideologies, so politics is generally default dinner conversation. A lot of my closer friends, from high school and especially college, are also extremely political.
I remember some great drunken debates with my fraternity brothers; almost everyone voted for Obama (except one guy, pre-law, southern to the bone with a Confederate flag hanging on his dorm wall, who surprisingly voted for the Socialist Workers Party ticket), but there was a notable divide between the leftists and the pro-business social liberals that always came up whenever something like unions, healthcare, or taxes came up.
But I'll honestly talk politics with anyone, if it's invited. For example, I had a great conversation just a few hours ago with a Peruvian guy who works with a friend of mine. I now understand the anti-Humala sentiment among Peruvian expats in the US firsthand.
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