Writing as a frequent visitor to this area from just inside the Ohio border...

Can't speak for accommodations or attractions, but the Dark Horse Brewery/taproom is in Marshall, barely 40 miles to the west. Some of the best brewpub action you'll find outside of Ann Arbor (but not as far as Bell's or Founder's in Kalamazoo or Grand Rapids).

Plenty of accommodations and attractions in Detroit....I can't go to a Tigers or Lions game without a visit to Slow's BBQ (again with a great beer list). Also the Cadieux Cafe on the lower east side is a gem if your boyfriend is into the whole Belgian beer thing....incredible Belgian food, too (mussels, et al). Michael Symon's Roast in downtown DTW (ignore the creepy post-apocalyptic 'does anyone live/work down here?' vibe) is also really, REALLY good.

1.) Garlic bread. Even bad frozen garlic bread.
2.) this one might raise an eyebrow or two, but it s from my childhood.....Campbell's Chicken and Stars soup and a bologna sandwich. Cut the sandwich into little bite-size squares, smoosh them so they don't fall apart, and drop them into the soup. Repeat. A rare occurrence now....
3.) Wasa light rye crispbread (or good seedless rye bread) with a smear of butter and some rolled-up ham.

Hands. Takes longer, but you have absolute control. And you develop Popeye forearms, so there's that, too.

If you can't get a Bayless reservation at Frontera/Topo, for the love of all that's holy, go to XOCO, Rick's sandwich place on the northeast corner of his empire. the food is absolutely jaw-droppingly good, and the fresh churros and hot chocolate made-to-order will bring you to your knees. Even for breakfast.

Yeah, got to go with Zingerman's. YES, it's a little on the expensive side, but they can also probably tell you the name of the cow your corned beef came from. If you're into that sort of thing.

I got a Keurig for work in an attempt to cut out my daily coffee runs to the local nautically-themed national chain that will remain nameless; it certainly isn't 'coffeehouse' coffee, but it's certainly better than the slightly caffeinated brown water they brew in my faculty break room. I also appreciate, as someone who left Oregon for a job in Ohio, that you can get Coffee People coffee pods; the Black Tiger isn't QUITE what it was in the Northwest, but a welcome enough reminder!

I had two great meals at Bar American (as in Bobby Flay's) last week, and observed several children of that age amongst the other patrons, having a grand old time. The staff is certainly warm and accommodating, and the food isn't <too> far out for an ambitious 8-year old (personal note: the Monday fried chicken special is really, really good).

Also, just because I never get tired of talking about it, the liege waffles from Wafels and Dinges waffle truck (different locations every day, posted online and Twitter) are about the best darn things I've ever shoved in my pie hole. I would have wanted to run away and join them, like the circus, when I was 8 or 9!

Hmmm.....want to show off Chicago, and I'll assume you don't want to go the Morton's/Ruth's Chris/ubitquitous a la carte steakhouse route...
Well, call me crazy (and I'm sure some holier-than-thou 'how dare you' foodie will), but I've never had a bad meal at Ditka's. Can't get much more Chi than that. Pork chops. 'Nuff said.