Blueberry Pie Guy

Photo by Oleg Magni on

How About We…

So there I was single girl in Chicago, trying to figure out how to find love. If you’re just joining us, you may want to go back and start at the beginning to see how we got here.

Since I still found myself mostly surrounded by women, gay men, or people outside my age bracket, I figured why not give online dating a try. The thing they don’t tell you is trying to choose a dating app can be just as hard as finding a decent date. Paying for a service like Eharmony and Match- ehh seems a bit too serious. A free app like Tinder- ehh seems a bit too casual.

Then, I stumbled upon a relatively new app called How About We. The general premise being that you suggest a few first date ideas in your profile to go along with the normal getting to know you stuff. This gave a nice way to find someone who might have similar interests as you, and coming up with a first date idea couldn’t have been any easier. Given what I know now about how completely awful some guys can be at planning dates, this was a genius idea from the creator. So I created my profile and off I went, searching, swiping, and winking away with the nervous, but excited hopefulness of an online dating virgin. One of my first memorable dates from this site was with a guy who was a cook. I will always remember him as the Blueberry Pie Guy. Here’s our story.

Go to the Zoo

One of my date ideas for this site was How About We… go to the zoo. In Chicago, there is a really nice outdoor zoo that is free. A brilliant idea for a cheap, but fun date in my opinion. I’ll admit I’m not really an animal lover, but strolling through the zoo allows plenty of time to get to know your date, and in case the conversation runs dry, there’s also the animals and people watching to provide opportunities to pick up the conversation.

So after exchanging a few messages, Blueberry Pie Guy and I picked a date to meet up and that was that. Unfortunately the day we chose turned out to be one of those disgustingly hot summer days. By the time I walked to the El, rode to the correct stop and made the short walk to the zoo, I approached my date already feeling the sweat rolling down my forehead and silently praying my deodorant did it’s job that day. I guess I didn’t really consider what a great first impression enormous amounts of sweat might make.

Despite the weather situation though, we had a decent enough time weaving our way through the giraffes, hippos, and polar bears, and wandering past the colorful birds and flamingos. We got a slight respite from the heat in shady areas and on a short stint through the reptile house. By the end of our date, we had sweat off a few pounds, kicked off some of the nerves, and had a potential for more dates. So I agreed to a second date, and then to a third.

Three Date Rule

Leading into the third date, we had yet to make much physical contact beyond a polite hello or goodbye hug, despite a bit of flirting. I was ok with things developing slowly, but also eager to get to some hand holding, cuddling, or kissing to see if the physical chemistry was there. At this early stage of my online dating career (yes, it’s basically become a second career now), I developed the 3 date rule which I still use to this day. It goes like this. I will go out with a guy up to 3 times if I think there is some potential. Even if the first date isn’t spectacular, I’m up for giving things a chance to grow, especially when first dates can be nerve wracking and awkward. If after 3 dates, things haven’t progressed, I will end it there. I don’t see the point in wasting my time or his. I’m not a serial dater just looking for a guy to buy her drinks and dinners, and my no-nonsense personality is certainly not one to keep people around just because. So as I prepared for this 3rd date, there was lot on the line.

We planned to head to the Taste of Chicago downtown for this date. He met me at my apartment, and greeted me with these impossibly cute mini blueberry pies (Hence the nickname). With the pies safely stored in my apartment, off we went on the el train headed downtown. The first strike on this date came when he didn’t have any idea what el stop to get off at or where to go once we exited the train.

Listen guys, if you’re taking a girl on a date, you should probably look up some directions for where you’re going or at least know how to use google maps to figure it out. Luckily, I knew where we were going and helped us set off in the right direction. We spent a couple hours perusing the various food and drink tents. We finally held hands a bit, but the chemistry wasn’t really cooking. As we headed home on the el, we approached the stop where I needed to change trains. Instead of wishing each other goodbye, he decided to come with me and walk me home. I’m not really sure if he was hoping to extend our date at my place or just being a nice, chivalrous guy, but it got a bit awkward when I was trying to say goodbye one minute and he’s following me on my train switch the next. Strike 2 when your chivalry turns kinda stalker-y.

After making it to my place and saying our actual goodbyes, he headed off. About an hour later, I get a text from him. “So when I left your place, I accidentally took the bus in the wrong direction and didn’t realize it until I was about 3 miles in the wrong direction.” Well, there’s strike 3. This poor guy has some serious problems with directions. I guess I should be glad he made it to my apartment on time in the first place. So the three date rule claimed its first victim. It may have been the first, but it certainly wouldn’t be the last.

Until next time,


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