Speaker A
Ah, this is our first date. Welcome to the Dating Files, the Dating Fail Files.
Toni and Ryan share hilarious dating fails and awkward moments in this TRY NOT TO LAUGH challenge.
Ask about this video. Answers come from its transcript only — with the timestamp, so you can check them.
Generated from the transcript and can be wrong — check the timestamp.
Key Takeaways
- Surprise plans on dates can lead to discomfort and immediate breakups.
- Clear communication about paying on dates is important to avoid awkwardness.
- Dating fails often involve mismatched expectations and social faux pas.
- Humor and honesty help navigate the awkwardness of early dating experiences.
- Chemistry between people can be electric and noticeable even in casual settings.
What the video covers
- Toni and Ryan recount their first date experiences filled with unexpected surprises and awkward moments.
- They discuss the discomfort of surprise exercise plans on dates and the confusion over paying separately or together.
- A story about a disappointing dinner date involving sausages and awkward expectations is shared.
- They reflect on the 'naked man' dating tactic and how it might be perceived in long-term relationships.
- The hosts joke about comfort levels with nudity around close friends and partners.
- They discuss the timing of breakups during long walks and the frustrations that can arise.
- Toni and Ryan comment on the chemistry between a man named Jordan Weir and a waitress, highlighting their excitement.
- The video includes humorous banter about crushes, misunderstandings, and social awkwardness during dates.
- Throughout, the hosts maintain a lighthearted tone while exploring common dating fails.
- The video is structured with timestamped chapters that guide through various dating anecdotes and reactions.
Full Transcript — Download SRT & Markdown
Speaker A
Ah, like my date didn't tell me we were going on a hike. Dumped immediately. What sneakers?
Speaker A
Oh, it's so cold. People that spring surprise exercise need to be put in prison.
Speaker A
Like, oh, so I just thought we'd run a marathon for our cat trap.
Speaker A
I'm like, oh, well no, no, obviously not. Are the checks going to be together or separate?
Speaker A
You're going to let me hit that tonight?
Speaker A
This is our first date. It'll be separate. Should we go out and make that?
Speaker A
Oh, were you guys paying together separately and you asked me? And it's like a gag. We don't do pranks, but... but you would say [ __ ] yeah.
Speaker A
I'm giving it all up.
Speaker A
And I'd be like, I'll pay. He's my Platinum American Express Cofe Char. As much money as you want.
Speaker A
So this guy invited me over for dinner at his place, and I got there and I got excited. Like, what are you making to
Speaker A
have an Emil day? And he said sausages, and I'm like, okay, that sounds pretty good. He went on his Wier a PL. Hope you're hungry.
Speaker A
Why is it so much worse when you do that again? I'm you're [Music]
Speaker A
hungry, and she goes, I hope you want a taco, and she pulls her pants down. She's my Mexican.
Speaker A
I'm sorry, obviously you're leaving that house right away and being like [ __ ] you.
Speaker A
Well, obviously not, because that guy sounds like the biggest [ __ ]. Has he gone to work that day going, I think I know my play tonight, you know what I mean?
Speaker A
Like, as he thought, all I'm going to do is all the [ __ ] love. It turns out it's none from 50 so far.
Speaker A
Oh, I bet it was a [ __ ] share house as well, and Danny who lives in the other room was in the kitchen. He went, yeah, nice sh Cocker board.
Speaker A
I know you're have my pickled onion, sweetheart. Sorry, I've gone too far, which is unlike me.
Speaker A
You're a fan of How I Met Your Mother?
Speaker A
Am, what do you think of the naked man?
Speaker A
Oh, I think it's bold. I wouldn't be very happy if someone did it to me. Like, for instance, you and I have been together for 10 years.
Speaker A
Imagine if he just like came out and was just like, upop.
Speaker A
But that's kind of funny, right?
Speaker A
Yeah, but also if I saw TOS naked, that wouldn't be strange to me.
Speaker A
Yeah, but if
Speaker A
but like because he's like deliberately gone and like got and come back out and been like, oh hey, what's up.
Speaker A
Yeah, yep. For some reason in my mind, we the Poo, I imagine you doing it like, 'cause I've never
Speaker A
seen you naked. Like, I've seen you mostly naked except for your swim sod area. Like, I've seen you in a Budgy Smuggler. I've like, I've seen you in your undies and stuff. It just sounds weird when you say it.
Speaker A
Sorry, sorry. Was it weird or was it not?
Speaker A
No, like it felt like normal because I've known you for a long time and I know you so well. In the Airbnb, when I got up and came into the kitchen and said, am I
Speaker A
wearing pants? And you and Sophie said no, and I went back to my room.
Speaker A
Well, you were talking to me and you were fine in your underwear, and then Sophie came out and you went, I should probably go put some
Speaker A
clothes on. And I don't know whether I should be flattered or offended by the fact that it was fine for me but not fine for our employee.
Speaker A
Actually, no, now it really is adding up.
Speaker A
Yeah, never break up halfway through an hour-long [Music] walk.
Speaker A
We've been like this for 20 minutes. Always break up when you either get to the destination or when you get home. This is just ridiculous.
Speaker A
Do you reckon her recording that video just like [ __ ] him off that
Speaker A
final bit?
Speaker A
Yeah, I do. Yeah, I really [ __ ] do. That would make me so [ __ ] mad. And, but imagine if his thing is like, you're into TikTok way more than you're into me, and she goes, that's not true.
Speaker A
He reckons. Can you believe?
Speaker A
Yeah, that's very kind of you. No stress. I feel good. I think we got along pretty, pretty well.
Speaker A
No, I've walked away from it knowing who she is as a person.
Speaker A
Sorry, I know that guy. Can you do me a big
Speaker A
favor?
Speaker A
Yeah. Oh God, I don't know what her name is. I've got the biggest crush on Jordan Weir, and he knows that.
Speaker A
What do you mean? He subtly like, I don't know it. I name, I don't know. You didn't get it, so now I'm
Speaker A
like, oh, it's too late now. Ask how she pronounces it.
Speaker A
Oh, they should go out. What, Kim? I can't help you. I don't know it.
Speaker A
Uh, oh, I'm so embarrassed. I want to say it's Elena, Eleanor, Elena. What is it?
Speaker A
Okay, do we have an
Speaker A
answer? So the chemistry though between Jordan and the waitress is electric. Honestly, like out of this [ __ ] world. They are definitely perfect for each other.
Speaker A
When Jordan and Mystery Lady were on the screen, I go, that no chemistry at
Speaker A
all. No, I can't believe. Sorry, I just got so excited about Jordan Weir being on the TV. Can we watch my favorite Jordan We TikTok?
Topics:dating failsfirst dateawkward momentstry not to laughToni and Ryandating storiesrelationship humornaked man tacticbreakup adviceTikTok crush
