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Advice: OK to pursue a guy if he's 'seeing someone'?

There is a guy I'm interested in, and I want to get to know him better. We have had a few conversations about basic business or networking. A friend of mine recently had a conversation with him and he shared with her that he is "seeing someone" and broke it down to say to her, "He's investigating that possibility still and is willing to go there if his investigation yields promising results" in regards to the girl he's seeing. My question is, would it be wrong or leading myself astray if I still attempted to get to know him and possibly pursue something romantic? I don't know him as well as my friend, so we have not had any personal or romantic discussions. I just know he seems like a great guy, attractive and has great values, and I really wanna see if I can take it there. I'm just wondering if I'm wasting my time since he is "seeing someone."

—Time-Waster

I will get to your problem, but first I must take issue with the fact that your potential beau described his current relationship as if he were a robot discussing seed germination. But, hey, to each their own.

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?"

Want to ask Anna an anonymous question about love, sex or dating? Email your quandary to redeyedating@gmail.com.  Need to give your dating life a boost? Sign up for RedEye Dating. Pick dates, not people.

Copyright © 2015, RedEye
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