Bonita,

I have a co-worker whom I get along really well with, and we have a lot in common. We've talked several times about hanging out. In fact, she's usually the one who brings it up. But then, when the time comes, she always gives me an excuse not to. What should I do? What is the point of acting like you want to hang out if you don't want to?

Sincerely,

Confused in Colbert

Dear Confused,

My first impression is that this woman certainly likes you and counts you amongst her friends, but perhaps she’s a little bit chaotic when it comes to organizing her life. I can be that way, for sure. I double-booked myself this week and only realized it last night, when I anxiously discussed business issues over an old fashioned at Flicker and then rushed my ass to a platonic date at Expat. (Go on dates with your friends, y’all. It’s so much fun!) I put everything in my phone calendar, which also syncs to my Google calendar, but somehow I just didn’t notice that I’d scheduled two events that deserved all of my attention within an hour and a half of each other. I had no excuse, so I just chalked it up to the game and dove straight into my overbooked evening. 

Now, the difference between me and your friend is that I have a woefully guilty conscience, and I’ll run myself ragged before canceling an obligation. I commend her for being honest about scheduling conflicts and not over-exerting herself like I constantly do, but unfortunately, she’s now established herself as a flake in your eyes, and personally, I’d rather be judged as too busy instead of someone who makes empty promises. Not good.

There’s also the possibility that she’s not actually interested in hanging out with you at all, but keeps organizing hangouts out of some sort of polite obligation. Canceling every time is pretty much the opposite of polite, though, so I doubt this is the case. She seems to like you and want to be friends outside of work, but this woman sounds like she’s just kind of messy and disorganized. 

Instead of letting her choose the time and place, how about you offer something up next time? She might be less prone to cancellation when someone else sets the date. Do y’all work anywhere near downtown or other public spaces? Try meeting up for happy hour immediately after work, or if y’all work second shift, you could share an after-work drink or bar snack. If you’d rather go straight home after work, maybe try organizing a group outing with other co-workers, or invite your favorite partner along—I am done with assuming monogamy for the masses—and make it a double date. Perhaps the prospect of more people being there will be more appealing for her.

If you’re petty like me, you could also just refuse her next hangout offer and tell her exactly why: “You keep canceling on me.” That would create an opportunity to speak frankly about her flakiness, and perhaps she would greatly value some commiseration on her hectic schedule or inability to commit. 

Truth be told, she’s probably fully aware of her flakiness, but I don’t think that undermines how much she likes you. I think her desire to spend time with you is sincere, but some people are just terrible at following through. Try scheduling a platonic date with her, or choose a can’t-miss event like a concert or a movie on opening night. I don’t see anything malicious in the person or actions you’ve described. I see a possibly overworked person who really wants to hang out with a new friend, but can’t find the time.

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