Digital Diaries Season 2 Episode 6: Northwestern students’ worst first dates

Erica Schmitt and Virginia Hunt

On Season 2, Episode 6 of Digital Diaries, Northwestern students reflect on their worst dates they have ever been on — and they try to offer advice.


ERICA SCHMITT: From The Daily Northwestern, I’m Erica Schmitt.

VIRGINIA HUNT: And I’m Virginia Hunt. This is season two, episode six of Digital Diaries, a weekly podcast following the college experience and asking students a question about life at Northwestern.

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ERICA SCHMITT: Last week, we talked with Northwestern couples about how their love started along the Lakefill.

VIRGINIA HUNT: But we all know college isn’t always roses and chocolates for everyone. In honor of the single students on campus, we asked Northwestern students to share some of their worst date experiences.

ERICA SCHMITT: Maybe to make you or anyone else wanting a Valentine feel a little bit better about those rough romantic experiences.

VIRGINIA HUNT: Medill freshman Ava Hoelscher reminisces on a bad date in eighth grade.

ERICA SCHMITT: Just a refresher for people who don’t remember middle school relationships: Picture emailing each other because you didn’t have a phone yet, sitting next to each other in the lunchroom and walking to class together.

VIRGINIA HUNT: That was Hoelscher’s version of dating her next-door neighbor. But their first official date was later on in the relationship, at a convent a half mile away from her house.

AVA HOELSCHER: He picked me up from my house — walking, obviously, because when you’re in eighth grade, you can’t drive. We walked hand in hand over to the convent because it’s actually, like, really pretty. A convent’s a nunnery so we were like, with nuns. But we walked down to like a bench in kind of a secluded area and talked. And we kissed, and it was my first kiss.


AVA HOELSCHER: It was not good. Like, really awkward, but he was very into it.

ERICA SCHMITT: And then they left. But Hoelscher’s story doesn’t end there.

AVA HOELSCHER: He dropped me off at my house. And then three hours later, I get an email from him. Because remember, like no phones, it was only emailing. So I get an email from him that is essay style, about how he believes in abstinence. And he doesn’t think we should go any farther, and he really loves me and values me, but doesn’t want to violate himself and like wants to wait until marriage to know that it’s, like, truly meaningful and, like, it was a peck.


AVA HOELSCHER: We literally were, I was 13. Sex was not on my mind. Like, literally had not crossed my mind.

VIRGINIA HUNT: How did you respond to that?

AVA HOELSCHER: I broke up with him.

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VIRGINIA HUNT: Weinberg sophomore Simon Roston had a memorable date during his sophomore year of high school. It all started with an Instagram DM from a girl he met at summer speech and debate camp.

SIMON ROSTON: She Instagram DM-ed me and asked me, literally word for word, to ask her out because her family decided that men have to ask out the woman because they were insanely Christian, which I did not know at the time. So we went to the movie theater and her older sister was there and she sat behind us in the movie theater and when the girl, like, leaned in close to me during the movie theater, her sister physically pushed me away. And then after the movie was over, her sister was taking her and said, “Just so you know, she is not kissing you or having sex until you’re married.”

VIRGINIA HUNT: Wait, was there a second date?

SIMON ROSTON: Yes, there was. I didn’t know anyone, I was going to a new school and she was a person I knew. There was not a third date.

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ERICA SCHMITT: Weinberg freshman Ronaldo Tineo was supposed to have a first date with a guy last weekend.

RONALDO TINEO: We agreed to like get dinner. Last week he texted me and was like, “Hi, like are you free this weekend?” and I was like “Yeah, like, of course, like, are you free on Saturday afternoon?” And he was like “Yeah.” So he goes to UChicago (University of Chicago), and I was like, “We should get dinner, where do you want to go?” And he wanted to get dinner in an area near UChicago. And I was like “Okay you pick the place because I’m like, not familiar with the area,” obviously. And he was like, “Okay, like, let’s just figure it out the day of the date.”

VIRGINIA HUNT: But the day of, Tineo was still unsure about the plan.

RONALDO TINEO: I was late, so I was supposed to get on the train at like, 6, I got on the train at like, 6:40. I texted him, I was like, “Oh, sorry, I’ll have to push it back to 9.” And then I sent him another text and I was like, “Also, where are we meeting specifically?” an hour passes, I’m still on the train and no response.


ERICA SCHMITT: Luckily, Tineo was staying the night at a friend’s dorm so he had a backup plan.

RONALDO TINEO: I get to her dorm and no text, still. An hour goes by. No text. Two hours go by, no text. My friend is like “Oh, let’s just go out with my friends,” like whatever. And I was like, “Okay, but like, that’s so messed up.” I go to sleep, the next morning I wake up and I’m getting ready, and I get a text and it says “Yo, I’m sorry. I fell asleep early last night, I was exhausted.”

VIRGINIA HUNT: But there’s no way.

RONALDO TINEO: But there’s no way. I understand if you went to sleep early, but there’s no way you were asleep at 7 p.m.

VIRGINIA HUNT: Do you have any tips for people to handle this situation or to avoid this situation?

RONALDO TINEO: If a man is not going to go above and beyond to have every second of the date planned, don’t go. Don’t go over there. I should’ve, like, made sure that there was a plan in place before I even decided to like take the train to UChicago because it is a long commute there.

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ERICA SCHMITT: SESP junior Lucy Joseph didn’t even get to the actual date, but the buildup was a story in itself.

LUCY JOSEPH: I was on Hinge, and I matched with this one guy and he was like pretty ugly and he was also 27. So we’re like talking a little bit, but then I was messaging him a lot and I was texting him through his email, so there was like a lot of red flags here. And then I invite him to come over to my house, to the party, and he kind of freaked out and was like, “I just, I think it’s too early to do that, I’d love to go out with you to a party further in the relationship.”

ERICA SCHMITT: He asked if she wanted to get dinner with him another night instead.

LUCY JOSEPH: The next day I was like, “Oh, I’m like really busy today, can we actually, like push it to Monday or whatever?” because I was like, “Uh I don’t really want to do this anymore.” I was trying to figure out a way to either cancel it or push it back again. Then I got a text from an unknown number saying “Hey, this is Jack. I think I left my wallet at your house at the party on Saturday. Do you have it?”

VIRGINIA HUNT: Joseph originally thought that this was one of the Jacks from the Northwestern crew team. It was not. In fact, it was the guy from Hinge trying to find out if she was ignoring him.

LUCY JOSEPH: I was like “Hey like, I’m sorry, I just don’t think I’m going to be able to go tonight.” That’s like all I said. And he was like “Oh okay, like how’s Jack doing?” I was like “What?!” and then I blocked him and I blocked the other number too because I was like “Oh God, this is terrible.”

ERICA SCHMITT: Do you have any advice for people in similar situations?

LUCY JOSEPH: If you notice red flags, don’t ignore your gut. Like my gut was telling me, “Oh girl, you do not wanna go on this date.”

VIRGINIA HUNT: You heard it here first: watch out for walking red flags.


ERICA SCHMITT: From The Daily Northwestern, I’m Erica Schmitt.

VIRGINIA HUNT: And I’m Virginia Hunt. Thanks for listening to another episode of Digital Diaries. This episode was reported and produced by me and Erica Schmitt. The audio editor of The Daily Northwestern is Erica Schmitt, the digital managing editors are Joanne Haner and Olatunji Osho-Williams, and the editor in chief is Alex Perry.

ERICA SCHMITT: Make sure to subscribe to The Daily Northwestern’s podcasts on Spotify, Apple Podcasts or SoundCloud to hear next week’s episode on Monday.


Email: [email protected]
Twitter: @eschmitt318

Email: [email protected]

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