Dating horror stories with Rachael O’Brien

stassi rachael dating 101

On this episode of Straight Up With Stassi, our girl is joined by her frequent guest and BFF Rachael O’Brien for Dating 101.


“It’s not like you’re like, a ho.”

“You are, and have been, an inspiration,” Stassi says to Rachael. “I don’t know how to word this correctly. Because it’s not like you’re like, a ho. You’re not dating a bunch of dudes at the same time seriously. But you go on dates all the time. Because you’re not serious with anyone.”

“Well, I’m trying to figure it out, because I’ve spent so many years in relationships, long-term relationships (four and a half years, then two and a half years, so let’s say it’s been seven years). I’m dating for the first time as an adult and I’m just trying to figure out what I like and what’s right for me,” Rachael explains. “Because I used to just like the first person that was nice to me.”

“Me too,” Stassi says. “Or the first person that went down on me.”

“Your story is a little different,” Rachael laughs.

“Either go down on me or talk about murder,” Stassi jokes.

“I said on my podcast the other day, ‘I’m like a community college, everyone can get in.’ Just say a few things I like,” Rachael says. “I don’t mean that in the slutty way… I just mean I’ll date anyone.”

“I’m gonna start calling you SMC: Santa Monica College,” Stassi says.

“Now I have a new standard that I want someone who is successful, but aside from that I don’t care what you look like,” Rachael says. “But I don’t want to be with anyone super lost. No one is going to be a totally whole person, but I don’t need to date someone totally lost. I don’t have the energy for it anymore.”

“Okay,” Stassi says, “great answer, Miss America.”


“Why make fun of someone when they’re being upfront?”

“Would you rather be ghosted or have someone be upfront with you?” Stassi asks. “Because most people would say ‘be upfront’ but then sometimes when someone is upfront with you, it’s jarring.”

“I did try to think about that when someone did that with me where I was like, ‘Well I didn’t even care, why’d he send that?’ And then I stopped for a second and was like, ‘Why make fun of someone when they’re being upfront and actually doing the nice thing that you would so much prefer?’ Of course being upfront is way better,” Rachael says.

“It is way better, but right now… So I was ghosted on every time, okay? No one was upfront with me,” Stassi says. “Meaning that all of the sudden feelings changed, but they wouldn’t tell me that they changed.”

“Yes, where you think it’s going one way and they’re all into you and they’re pouring even more into you than you would think and then all of the sudden it’s like…”

“‘Woah, pump the brakes,'” Stassi finishes Rachael’s thought. “And acts like, ‘I’m just going through a lot right now…’ No! It’s bullshit. You were just stringing somebody along.”

“Which is horrible to do to girls,” Rachael says.


“Honestly, he can suck it.”

“The point of this whole dating thing is: Would you rather be ghosted, or have someone be upfront,” Stassi says.

“It depends on how invested you are,” Rachael says.

“Maybe guys and women aren’t assholes for ghosting, because they don’t want to hurt someone’s feelings,” Stassi says.

“But sometimes it hurts your feelings more though, because you’re like, ‘What did I do?’ But then with the upfront text of like, ‘I’m just not really feeling it,’ you’re like, ‘What did I do that you’re not feeling it?’ I can’t say which is worse,” Rachael says.

“Who have you lost the most sleep over?” Stassi asks.

“I’ve lost sleep over none of them, frankly,” Rachael says. “I would say that there’s one of them that I didn’t like as much even though I knew him longer where I was more offended [when he was upfront], like, he tricked me. And we were also doing this pen-pal shit for weeks and then he sent me that. That’s why my response was, ‘Oh, I know.’ It wasn’t, ‘Oh I know, I’m better than you,’ it was, ‘Oh, I knew you didn’t like me, you can stop pretending to.’ That felt more demeaning in a weird way.”

“I agree with that one, I understand,” Stassi says. “The longer you’ve had time with someone and they’ve actually put in so much effort and brought you fucking dessert and all of that shit, it’s like, you’re tricked. You don’t just do that.”

“But, you wouldn’t have been my choice, but you made me feel loved…”

“Honestly,” Stassi says, “he can suck it.”




No Comments Yet

Leave a Reply