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I personally love Riesling. Is it a Riesling from the Northwest? a German Riesling? Its wine that beginners can enjoy, because of its crispness and fruitiness (yes... some people look down on it... but Riesling really is the king of wines, especially for bringing out the terriore of where it is grown.. )
It might be overpowered by the chocolate though. Port or sherry might be fine, but if she's not really into port or sherry, she might not like it. Its a hit and miss kind of thing with port or sherry.
Shiraz/syrah is a pretty full-bodied/spicy type of red that goes well with chocolate. Talk to your friendly wine-store guy, and see what he recommends.
You might want to start with the Riesling, and some cheese, then go into
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