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Dating with apps | Jeff’s diary

The 47-year-old keeps a diary of dating using Scruff, the app for meeting gay men.


Dating via app Jeff, 47, Edgewater, gay

Jeff uses the Scruff app, which locates other Scruff users (read: available gay men) in real time, to chat and meet up with guys in his neighborhood, or to just make new friends. “A neighbor (whom I met on Scruff) and I have the same philosophy: Let’s meet our single neighbors, get together every couple of weeks and introduce everyone,” Jeff says. “I think it’s a lot easier to get to know new people in a small social gathering rather than in the one-on-one dating hot seat.”

December 14 Lots of activity on Scruff. I had a message from a guy who was passing through Edgewater on the Red Line, and I exchanged phone numbers last night with a medic who lives in the building across the street. It would be easier to invite him out for drinks with the guys next time around.

I also checked on the guy from Wheaton who just moved to the neighborhood. We’d met and had a Sunday-afternoon date about a month ago—we still hang out from time to time. Got a text from a buddy in Rogers Park about meeting at Big Chicks tomorrow night for a friend’s birthday. Sent a message on Scruff to the guy who moved here from Minneapolis to see if he can join us.

Also saw on Scruff the very handsome neighbor whom a friend had tried to set me up with in the summer. After days of rampant texting back and forth in June, he now won’t even acknowledge an online hello. The electrician in Rogers Park texted and said that a Sunday-afternoon movie might be in order. We’d met previously but started hanging out together only after my neighbor across the street brought him to one of our “meet the neighbors” nights at the local watering hole.

December 15 Checked in with the banker from Evanston on Scruff to see if he’s still up for getting together for a drink on Saturday night, then caught the bus up to Big Chicks to meet up with some friends for that birthday party, two of which I know from Scruff. Fun night, but it was a major buzzkill when the ex walked in. It’s not like you can evade someone at Big Chicks.

December 16 I’m hoping to meet up for drinks tomorrow night with the banker from Evanston. It’s our second attempt to get together—the first time he had company in from overseas and it made sense for him to spend time with those folks. We’ve talked for a couple months now after having met on Scruff. Now we text and/or use FaceTime to chat.

December 17 Slept all day after being nailed with a cold, and had to cancel drinks with the banker.

December 20 The electrician from Rogers Park came by for dinner. I made lasagna and brussels sprouts, and we had French bread and red wine. It’s always a risk to prepare brussels sprouts for a date—they either love ’em or hate ’em. He said he wasn’t a fan but ate them and asked for more. Maybe brussels sprouts is the test. After all, if a guy is willing to try something he knows he doesn’t like, maybe he’s willing to try more! Finished the bottle of red then moved to the sofa, put on a movie and uncorked another bottle.

December 22 A cold, dreary day is perfect for an afternoon coffee with a new face, so I used OkCupid’s Local app for a few hours. This reminded me of going fishing with my dad. He kept his fishing boat at my grandparents’ house, which was on a lake. Every time my dad and I went out fishing, we’d sit for hours just waiting for the bobber to move. I swore that lake had no fish, and that’s exactly how I felt about the Local feature today. Not once did my bobber go down.

December 25 The salt-and-pepper-haired man from Andersonville chatted me up on Scruff tonight. Decent conversation without the usual come-ons. Refreshing!

December 27 Chatted for hours on Scruff with a guy in Skokie. Lots of fun discussing our childhood. Handsome fellow and a nice conversation.

December 28 Received a message from the most adorable Polish guy on Scruff. Lives in London, unfortunately.

December 29 Wrote a letter to the electrician in Rogers Park describing how I’d like to explore something more together. Letters like this are better in print than they would be in e-mail. Sometimes you have to hold words to understand them better.

December 31 The salt-and-pepper-haired man sent me a message on Scuff today and we’re meeting for New Year’s Day Bloody Marys tomorrow afternoon! I was just telling a friend of mine how much my social life is now rooted in this app. For a number of my local acquaintances, this has become our primary communication tool.

January 1 Best first date ever! Salt-and-pepper man was right on time and we sat for hours sharing stories with lots of laughter. Despite the fact that we work in completely different industries, there are plenty of connections in our lives, past and present. Nice to have a date with a man my age for a change. (It seems to me that the largest demographic of datable men are typically in their late twenties to mid-thirties.)

January 3 Date No. 2 set with the salt-and-pepper man: dinner at my place on January 7. Pork cutlets with jalapeño-apricot glaze, baked potatoes and green beans.

January 4 One of the guys I chat with regularly on Scruff asked if I had a profile on one of the other dating sites. Once upon a time I did, and then I realized that despite being online for years, I was no longer meeting anyone in person. Rather, all of the relationships I had with people were keyboard-based—and that wasn’t my idea of meeting people. That’s when I pulled the plug on most of my online profiles. Even now while using Scruff, if the guys I chat with aren’t willing to meet, I start winding down the conversation rather quickly.

Got a call from the electrician in Rogers Park regarding the letter I’d sent. He was polite as could be, but he said we’re on different pages with regard to our time spent together. Not what I’d hoped for, but at least he was honest and forthcoming.

January 7 Best second date ever! Salt-and-pepper brought a bottle of Côtes du Rhône…my favorite! Following dinner, we listened to a recording of Sandra Bernhard at the Castro Theatre, then Teri Garr’s story she recorded for the Moth podcast. His lips were perfectly kissable—I stated that in a text while he was in the taxi heading home. “Likewise,” he replied.

January 8 Got a message on Scruff late this evening from the medic across the street. The guy he was dating broke it off. He said he was heading out to have a beer and asked if I wanted to come along. Had to decline due to an early wake-up time the next morning but chatted back and forth for quite a while. He’s a good guy and I’m glad we’ve become friends.

January 10 Logged into Scruff this morning to see if the medic across the street was awake yet. Considering his recent pitfall, I thought I’d invite him out to coffee. A few minutes later, he sent the message: “Breakfast?” We met on the corner and walked over to the diner. There’s something to be said for good, reliable neighbors who have weekdays off.

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