Thanks for that awesome post. I'm going with my girlfriend so I'm sure she'll love the paddleboat ride idea. I'd say we'd be looking for a combination of touristy and college/new grad stuff to do. Any particular recommendations with that in mind?
Paddleboat ride -
Tidal Basin Paddle Boats (really cheap for such a pleasurable experience!!)
Quick tip: pick her a few cherry blossoms on your way there and you are guaranteed to get lucky that night, haha, j/k
Gosh, it's been a while re: the college/new grad stuff but I'd say in terms of bars, stick to alot of stuff in Georgetown or near American University (in Tenleytown) and you can't go wrong.
You may also want to check out Buffalo Billiards which is actually kind of cool.
Buffalo Billiards DC
There's also a cruise too that provides a really nice view - you can check it out here:
Washington Cruises, Washington Dinner Cruises | Spirit Cruises in Washington DC
(Spirit of Washington)
Dinner Cruise Washington D.C. on the Potomac River
There's also the
National Zoo which isn't too far from where you'll be staying.
You can walk around and shop in Chinatown which has some really cool bars and restaurants and shops that has popped up lately.
There's an imax too
Smithsonian IMAX Theaters & Einstein Planetarium
(gosh this sounds way fun, I'm enjoying just thinking about the awesome time you guys will have - now's a way cool time to be in DC before that God awful heat kicks in :s)
You said your driving right? Honestly, you could probably drive around if you wanted as parking is nowhere near as bad as say NYC downtown but you guys should probably grab one of those DC Metro passes for the weekend so you can just walk around and enjoy each other's company, the sites, etc. without the bother of parking. Also, there are all these connector buses that will take you from the heart of Georgetown to almost all of the touristy parts.
If you want to go "off the beaten" path a bit, you guys can hit up U street which is kind of like...hmm let me think? Perhaps the village in NYC. You can go to Ben's chili bowl which is fun! I took a Swedish friend there about 3 years ago and she was all like "wow this is awesome", lol, like she was in a Spike Lee or Will Smith movie or something, lol.
[ame="http://www.youtube.com/watch?v=5fmd-rWDbkY&feature=related"]YouTube - Broadcast Yourself.[/ame]
If you see Obama there tell him I said hi, lol
Have fun!
Oh, ps you may want to check out what's at Ford's Theatre, The National Theatre and/or The Kennedy Center!! Sometimes they have deals.....
It's "our" capital so make sure to partake in the wonderful, high quality free things to do as well

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pps
here's a cool vid of close to where you'll be to. Don't forget the Lincoln Memorial!!!
[ame="http://www.youtube.com/watch?v=hZq0uGb2rlU"]YouTube - Broadcast Yourself.[/ame]