It seems like his relationship isn't super serious. He's not using the word "girlfriend," and he's exploring his options, so basically he could go either way with this girl. That means he's fair game, but don't hedge all your bets on him. Approach the situation casually, pursuing him the way Garfield pursues lasagna—do nothing until it appears under your nose. Often I'm against this lazy, inactive approach, but there are too many unknown factors in this scenario to support a full-scale pouncing, like whether he's monogamous with this gal or not.
Still, learning new things about people you want to date is never a waste of time, even if you never end up going out. Get to know him better. Hang out with him. Discuss more "basic business" and "networking." After that, if you find yourself really pining for him, but he doesn't show any signs of ditching his "investigation," you might want to distance yourself from him romantically. Alternately, you might get to know him better and figure out he's a giant douchenozzle. No one can say for sure, least of all me, all-knowing sleuth of what was revealed in that one paragraph up there.
So hop to that. But try not to, uh, hop ON that, i.e. have an agenda. Approach your "investigation" from the vantage point of "Let's see where this goes" and not "THOU SHALT BE MINE." Also, stop with the third-party snooping. Don't let your friend do all the dirty work. Go straight to the source. Ask him to enjoy a refreshing beverage with you in one of Chicago's delightful beer gardens (or one of the many other hookup spots we so thoughtfully researched for you!). Once you have some cursory knowledge about your paramour, or para-bore as it were, you can hit the meatier topics, such as, "So how's about them annuitization options on that acceleration clause?" Or, you know, "Are you seeing anyone?"
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