Remember the Older Dude from the Circular City Week events, with whom I drank to escape Phabio? (By older, I was assuming early 40s.) He and I professionally kept in touch, and got coffee a few weeks later. Then, in May, he invited me to grab day drinks in our neighborhood. Unlike my friends, I wasn’t sure if he meant it as a date; but just to be clear that it wasn’t, I wore no makeup and told him I had to go grocery shopping afterwards (which I did!). Despite a lower-back-touch that I had to quickly wiggle away from, and a declined invitation to continue drinking on his roof, I think I did a pretty good job of establishing our friend zone. I deflected a few follow-up invites, and then didn’t hear from him again until he asked me to get drinks last weekend. He’s cool, and I assumed our age difference was enough to solidify the friendship boundaries, so I accepted. (His age has since been confirmed as 46.) Unbeknownst to him, we met up after I’d spent the afternoon drinking multiple tiki drinks at my friend’s party, but I think I managed to come off as deceptively sober. After two cocktails that I definitely didn’t need, he walked me to where I was meeting up with some other friends. He left, and we girls got ice cream! It was a perfect day of friendly socializing.

The next day, he texts me:

Nice to see you last night. How was the rest of your night? So, the few times we’ve met it’s been in this somewhat professional zone. However, I’d like to take you on a proper date sometime. You’re lovely company :)

Before you say “aww,” you should know that he has a roommate—an automatic loss of points for anyone trying to date me. Plusssss, I have the rest of my life to date 40-somethings—and only an ever-shrinking window to cradle-rob 20-somethings!

I responded:

That’s very sweet, but I have to decline. I’m interested in someone else right now.

He said:


And that was that!

Who am I actually interested in? The Psychiatrist (31), who won’t text me back or make plans to see me again—of course!


Remember when I said I wouldn’t be able to see Phabio anytime soon because I was all booked up this past week? Well, I was hobnobbing at a bunch of Circular City Week events, and it turns out life is super creepy because I ran into him at one on Thursday. Coincidence? Stalker? I just didn’t want him harshing my hustle or whatever-the-professional-version-of-cockblocking-is me. So we chatted and sat next to each other, but I made it clear I was there for business. (At one point, he asked if I wanted his help talking to people—which I found weird and condescending mainly because he has fewer ties to the industry than I do—and I enthusiastically declined.) Apparently we’d been at the same event on Wednesday (where I met a cool older dude with a professional quandary similar to mine), and we were both going to the closing celebration on Friday.

Last night, I was running late, and Phabio texted to ask if I was still coming to the event. I eventually got there, quickly said hi, and lined up to cash in my drink ticket—where I made some new connections. After emerging from three separate conversations, I made an effort to go find Phabio, but he was busy, so I made myself a pitiful dinner from the picked-over snack table. I was soon ensnared in a new dialogue, when he comes over and EATS A CHIP FROM MY PLATE WITH A SMIRK. I told him he’s not welcome to my food, and declined his request for a hug—all in front of the poor woman I was talking to. They start chatting, and the guy I met on Wednesday magically appears. Drink tickets have run out and he suggests we spend our money on legitimate cocktails at the hotel’s lobby bar. I agree and we skedaddle. We get our drinks and chat for a while before I leave to meet my friend. During this, Phabio texts me asking if I left. I respond when I leave, and he asks me to dinner next week. I decline and tell him I’m not feeling a romantic vibe with him. He says he picked up on that because I was rude to him (??), but also asks why. I tell him it’s a gut feeling, but he continues to ask if I’m open to a romantic possibility. (Not sure why if I’m apparently so damn rude!) I tell him no, and he asks if I’m hung up on someone else or if he’s just not my type. I tell him I’m not really in a dating mentality at the moment (which is true, in addition to the fact that persistent and insulting isn’t my type), and he thanks me for being honest and finally says he’ll step back but to let him know if I change my mind. Not likely.