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Does she like art? If so, it's a First Friday in Raleigh. Many of the local galleries will be open and serving complimentary wine and snacks. It could be nice to stroll around and hop from place to place. You could start out at Art Space (they're may be a band playing in the Market area), walk over to the galleries in the alley just behind it, then head over to Sitti (nice looking space, won't break the bank, good Eastern-Med with small plates that are good for sharing) for dinner (or Duck and Dumpling) and have an after dinner drink on the rooftop at Busy Bee Cafe. Or, hop on a bicycle taxi and take it over to Glenwood for a drink at Solas. And, don't worry about Moore Square at night on the weekend (especially then), it's fine.
I like Solas, but I feel like it's a "bit much" for a first casual date experience.
I do like the First Friday suggestion though. Don't forget about the R-LINE as a means to get around downtown. It pretty much hits all the art districts. It's also a bit more reliable than having to track down a rickshaw driver.
How did I miss that you were talking Friday? Yes, First FRiday of course. Be aware of this too: Artspace | LoPop Shop (http://www.artspacenc.org/LoPopShop.html - broken link) at Artspace.
All these are good options. All are open and doing great. I LOVE Rockford, the only issue is that it can be pretty smoky as the evening goes on.
Zely and Ritz is one of my faves, but it can be pricey. It would be the quieter of the ones listed, though, but not in a bad way. Depends if you are looking for a "light" evening, or want to actually talk. Jay, the bartender at Zely, if one of the best in town, using all natural ingredients for his cocktails, not bottled mixes like most others. Yummm...
You didn't mention warehouse district, but my best recommendation would be Humble PIe. They have such incredible outside seating, including a great tiki bar with fresh fruit drinks and the best homemade pina colada in town. As beautiful as it has been outside, this is a great choice. The food there is really wonderful too.
hmm, i hadnt heard of humble pie. it looks really good. now i want to go there. 6 dollar martinis tonight, according to their website. and it IS nice outside. hmm....
[also, zely and ritz was a little expensive, but it didn't strike me as overpriced because the food and drinks were really fresh and whatnot. definitely liked it, though]
Tir Na Nog, nice, moderately priced Irish restaurant right on the square would be a good choice. For more casual experience, I like MoJoe's, right next to Mellow Mushroom (good veggie burgers, and those with actual meat) but that would probably be more appropriate for the second date.
The Boylan Bridge Brewpub would also be a good choice, casual, not pretentious, really good beer.
Mellow Mushroom is nice too, but it's good to go somewhere uniquely Raleigh on a first date. Lilly's Pizza in Five Points isn't necessarily "romantic", but the good pizza and atmosphere would be enough to impress your date!
There are many more options, but those are just my favorites.
Hey everyone - thanks for all of the amazing recommendations! Sorry I wasn't able to reply before now, but I did get to read all of your great suggestions before my date last night, which went great! I ended up taking Clever User Name's advice to check out First Friday (which was the perfect casual environment to check out art, have a few drinks, and listen to live music) as well as NRG's suggestion to go to Duck and Dumpling afterward for dinner. Can't thank you all enough - the bar is now set pretty high, but fortunately y'all have given me a whole list of other ideas for future dates. I'll keep you posted!
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