Love and Laughter in Los Angeles: My Low-Level Dating Horror Stories
Love and Laughter in Los Angeles:
My Low-Level Dating Horror Stories
Hello curious ladies curious gents: I have recently been dating in Los Angeles and I have some tea for you with some hilarious, personal experiences. I will record videos and blog about it below.
My goal in sharing my experience is to let you know, you’re not alone….enjoy a good laugh, and truly shine a light on a single woman’s experience trying to find to long-term relationship in the City of Angels.
Dating is a hilarious experience with lots of up’s and downs. It shines a light on the human experience as the true desire that want to be loved but we are also flawed, get triggered, and come with a past [that can influence our future] and somehow we fumble our way imperfectly through!! Such is the joy of life!! Being imperfect and basking in it!!
I want you to know that life is enjoyable, hilarious and worth living over and over again. In the long run, I do not see it as a failure if I am single or in a relationship. I only want to live my life intentionally, grow, have fun and keep learning [because I’m not freakin’ dead YET].
So let’s get into my dating experiences!!
My Hinge Strategy (Yes, I’ve Been On Over 50 First Dates)
I use Hinge as a heterosexual female, who is looking for a long-term relationship. Hinge is the #1 app in LA based on asking literally everyone I know, and all my friends!! So I would say this is an accurate assessment ;)
It’s my Hinge profile!
As a single female in Los Angeles, I believe that men who are dating should “Like” my online dating profile first, and that my job as a female is to go through my “Likes” List and Match with people who look (1) minimum average looks and I can imagine potentially getting to know and kissing; (2) that their profile and values align with mine; or (3) if their profile is lacking in content, then I am at least curious to get to know them more. Thus, I would say this is a reasonably low bar.
You know what they say… the odds are good but the goods are odd LOL. Which is to say, the number one complaint I’ve heard from single LA women using Hinge is… I don’t like any of my Matches (yikes!!).
My Hinge process is as follows: I go through my Likes. I like from my Likes List which creates a Match. From my Matches, we then engage in messaging. After a few messages, if they do not seem crazy, I then bring up, “I would love to tell you more on a phone call! [insert phone number] I trust you know how to use this…” or something along those lines. I try to keep the messaging light, flirty and fun.
Generally this is my Dating Process with Hinge: Likes > Matches > Messaging > Phone Call > In-Person Date. I won’t go any deeper on this strategy, as I will write a separate post on my own ideology of the dating funnel. (Can’t wait to share this with you later!!)
In case you need credibility, in the last 6 months, I have been on over 50 first Hinge Dates!! So my experience comes from someone who has had a freak-load of dates in a short time frame!! So I do speak from experience, even though I am technically new to the single pool.
The Beach Bum with No Career In Sight
Video of my summary of the Beach Bum date, originally sent to my personal friend, but I am sharing it with you too, as it’s an honest summary of how it’s going out here, dating in LA! I do spill the tea :D
This one is my favorite recent story because when I retell it, I keep laughing!! I don’t recall ever meeting anyone who brought the bear minimum (the sub-basement floor, honestly) to the table but yet ask for qualities in a parter that he himself didn’t appear to foster or hold on some level. It leads me to believe his is not self-aware at all and has never really had to hold a candle to himself! It’s not my people, as I can’t relate to someone who just doesn’t seem genuine…
So the first time I see him, he’s wearing flip flops (yes, I can see his toes), shorts, and a t-shirt with a standard black puffer jacket. He looks like he just got back surfing on the beach, and doesn’t give two sh!ts about making a good impression. He is the definition of beach casual and giving zero f**ks. And this annoys me. As I put some thought into my outfit and appearance, while I am not business casual in any sense of the word, I just want to present myself in a way that is genuine and appealing for a first meeting. I think my date is presenting himself genuinely; however, it doesn’t align with my vibes.
I knew immediately: if I were to see him in a bar or out and about, I would 100% keep walking and not look twice in his direction because I can tell, we are not aligned in values. So my first thought was, “Damn, I do not want to see him again.” But, I like to get to know people, and I commit to might-as-well having fun as we’re both already here. So let’s dive in!!
The date begins. First off, he misread my text inserting words that I did not say… so he had a confused, aimless look on his face. Not attractive. He holds up his phone, and then re-reads the text, but he doesn’t seem to get that he’s in the wrong. This low-level annoys me. UM, read the text! I told him I was waiting next to the indoor plant. He misread it as, “I’m waiting next to the plant store” WTF. He does not apologize for his confusion or misreading the text. This seems odd to me. This is not a difficult task…
We both order coffee, I assume he will pay. He is acting in a way that I feel, he does not want to pay for the drink. I do not care. The cashier rings up the total, and I make no motion to pay. He pays (praise be!). I am from the old-fashioned school where, if you do not want to pay for your date, then don’t date. It’s about respect and the desire to value and appreciate my time. It’s not about money. It’s about generosity of time and spirit, and basically, I expect you to play old-fashioned gender roles when it comes to the first date check. And it’s just coffee. This is not a big deal to me.
We sit outside. He talks about himself, and we go back and forth a few times sharing. This is what I pick up:
He does not work. He does not financially support himself. His parents are retired, and still living. He lives off of his parent’s money; they pay him [what I interpret] is a monthly stipend.
His parents are not poor. They had a house in Pacific Palisades, but it burned down in the January 2025 wildfires, and he is getting “paid” to oversee the re-construction. He mentions this several times to drive home the point that he is doing something of value. But from his schedule, I can tell this is not a 40 hour/week job… I think he helps and is handy when he wants to be. I gather this because he talks about camping often, and doing long, out-of-town road trips with him and his dog.
He rents a two bedroom apartment in Brentwood, which is not a cheap area. This means his parents must be paying him at least $4k/month, as I estimate the apartment is about $3k/month.
He has a 16 year old daughter. He is 44 years old.
I start asking him about his past relationships. He mentions, he just got out of a 5 year relationship with a 51 year old woman. It ended because she wanted kids right now, and he did not. Later, he admits, he DOES want more kids — just not now… maybe in 5-10 years. Which is shocking and appalling to me as old sperm increases the risk of genetic issues like autism… and I am thinking no one wants his old sperm when he is already in his mid-forties. :O Secondly, this is surprise to me as I list in my Hinge profile how I do not want kids. I verbally echo this by responding, “I don’t want kids…not now, not ever.” But he does not seem deterred which is odd to me.
He concludes, “I am just looking for more spice.”
I ask, “What does more spice look like to you?”
Him: “I don’t know.”
I am shocked by this answer as that means he literally talked about nothing and doesn’t know what he wants or he just doesn’t want to share which is odd… as this is a date and the goal is to get to know each other.
The biggest laugh was when I asked him, “What qualities are you looking for?” / Him: “Someone driven… and independent.” This makes me laugh because it is contradictory to the qualities I see him exhibiting. He does not mention building a career, and he has not held any job longer than a year. He does not have his own income… I interpret this as, he has a limited amount of money he gets from his parents and he does not want to share it! In my mind, I can’t see what he brings to the table other than his money! I do not see him contributing to my life in any meaningful way.
The final kicker, was when he explained… he is looking for something casual to start. I am 100% not looking for anything casual. I am looking for early intentions of a long term relationship. So this annoys me again, as this clearly lists this on my profile… and I think he thinks it’s merely a suggestion or he never read my profile (both conclusions annoy me).
Final text exchange with the Beach Bum…
I did end up going back to the counter and ordering food (I paid for it myself, as I knew I was not going to see him ever again), as I figure if I need to listen to this dribble, the least I can do is eat so I’m not hungry when I get home [as I am not a good cook, so eat most of my food out!]. Once my food was done, I was running late to another appointment so I race off. He offers to walk me to my car, and I decline citing that I am already late and need to leave now.
I resolve that I will not text him when I get home. While he paid for coffee, and did make the effort to drive to my part of town… I am now thinking that is the bear minimum and I do not want to encourage him…
However, he texts me an enthused, “Hey! Thank YOU!! That was nice. I’d like to see you again some time.” This confirms that we are not on the same wavelength…
I text back a final, “While I enjoyed getting to know you, we’re not aligned on future goals like kids, or relationship style so I wish you the best on this new round of dating!”
His reply: “I hear ya. Pleasure. Good Luck!!”
Thus ends, my most un-aligned date perhaps ever. Where he thought it was going well, and I was for sure wanting to run away as soon as possible!
Lessons Learned:
I don’t know! I did get on a phone call with him… but we had a normal back and forth and at the time, it was not clear that he was 100% living off of his parents. It was only when we met in person and he dove deeper into his activities that it became incredibly clear that he was truly a beach bum and had no income of his own. I didn’t want to outright ask how he made money, as that’s a little too close to the bone for the first phone call.
The biggest learning was that he looked very casual (beachy) in his profile pics… but we live in Los Angeles… and I just figured in his free time he was a surfer. I did not realize that he’s a surfer whenever he wants as he has such a flexible schedule and way more free time than the rest of us.
He was nice enough. But I just did not respect and admire him. I cannot date someone I do not respect and admire… thus onwards and hopefully upwards! Even if I stay single, I 100% benefit but not having that kind of [IMO aimless] energy in my life . We are just not aligned.
The Radiologist Who Wouldn’t Pay For My Coffee
My video rant about how the Radiologist didn’t pay for my coffee. Honestly, this may be the only thing I remember about him forever.
Apologies for the navigation voice in the background… I had places to be.
The headline pretty much says it… I went on a date with a high income earner (the top 5%, I estimate) and he did not pay for my coffee.
Wait… Is He Seriously Not Paying? I am shocked, annoyed, flabbergasted. Livid!
If I had known he was not going to pay for my coffee, I would not have agreed to meet him. We should just be very clear…if you do not want to pay for my coffee or meal, do not ask me out!
This also highlights the struggles of dating in LA. I was dating more creative types who generally do not have money, and I was complaining that it really was putting a strain on the relationship… and one friend nonchalantly advises, “You should date doctors and lawyers! People with money!” WOW, they have the whole scene wrong.
UM, it is an obvious statement; don’t we all want to date wealthier than us? However, on Hinge, most of the high-income earners are behind “Rose Gate” which means you have to buy a rose and offer it to them! These profiles are in high demand, and it’s very difficult to get their attention and get the app to serve them to you. Secondly, I tell them this Radiologist story…. about how I do manage to go on a date with a high income earner, and he very clearly refuses to pay for my coffee! What a turnoff.
The moment he refused to pay for my coffee, that was the moment that no matter what else we talked about, no matter how I felt around him - the only thing I could clearly remember was that he did not pay for my coffee hence I would absolutely not be seeing him again. I honestly do not care if you looked like Ryan-freakin’-Gosling. If you do not pay for my coffee, I will interpret this as you are stingy and un-generous and I do not want to be around that energy.
To put that in perspective, I’ve gone on over 50 first dates in LA, and when all but one of them pays for coffee or the meal, that puts this guy on the bottom 2%! This is unheard of in my book!
OK, now that I’ve gotten that rant out of the way, I will describe to you in detail, exactly how he refused to pay for coffee.
We go to an Art Gallery in Santa Monica, which he found and suggested. He wanted to check out the artwork, [the artwork] was actually kinda disturbing and creepy, but I don’t want to get into that…We see the artwork. It was a holiday weekend, so many of the art galleries were closed. We wandered a few art galleries, and it was fine. We didn’t talk that much as we were next to art.. and generally made small talk about which art you liked more or less and why. Honestly, I found the small talk boring.
Since I used to work around the corner, I offer up, that there is a coffee shop nearby, as there is nothing left to do in the art gallery compound - so let’s just sit down and chat. While we’re walking there, we discuss what kind of books we’re reading. He’s into SciFi. I am not into SciFi. He named a few series that he was deep into, and I decidedly know I would not like those books (too intricate of a read for me on my leisure time).
We walk to the Bluey’s Cafe in Santa Monica. It’s the kind of coffee shop where you order at the cash register, and bring your order number to your table. So it’s easy to split the bill…I step out first and order a cappuccino. The cashier announces the total like $6 buck-ish, and I turn around to look at the Radiologist (who is still in line behind me). He is averting his gaze, clearly NOT wanting to pay.
We do not exchange any verbal messages at this time…but I am shocked he does not step up to pay and when I look at him, he plays dumb. I am not dumb. I know what this means. I pull out my credit card, and for the very first time in my life, I pay for my coffee on the first date. Now in the past I’ve paid when I’ve offered (like when I know, I never want to see this guy again). But this time, I did not offer to pay and yet here I am stuck with my own bill! This is a new experience for me. I am livid. I mentally decide: I will never see this guy again. There will be no second date.
I cannot believe someone in the top 5% of income earners wants me to pay for my coffee. It would literally mean nothing to him! I’ve had people who cannot even afford a car in Los Angeles pay for my meal on dates…the lack of generosity is atrocious to me. The fact that I know Radiologists make at least $300K annually (which is 5X the median income in LA) is making me more mad. How can someone, so well-off, be so stingy! This is a new low.
I push aside my feelings. We sit at a picnic table outside. He ordered a coffee and avocado toast. He eats his toast. I drink my coffee. We continue our very unmemorable conversation. I have appointment to get to so we finish, walk back to the art gallery and I get into my car and drive home. That is when I film the above video, where I summarize my initial reactions.
Final closing texts with the Radiologists. I shut it down. He asked about one of my mentioned weekend activities, and I did not want to talk to him further.
In the end, I did not text him a thank-you-for-that-date text (as I usually do). I reason, well he did not pay for anything. We met at an art gallery, closer to him. He picked the art gallery and activity… I have nothing to thank him for. He’s the one who asked me out…He later texts me, asking about one of my prior mentioned weekend activities.
I wrap it up, by lying and saying - hey, we should be friends… instead of actually saying, “Hey dumb@ass, you need to pay for your date’s coffee on the first date otherwise you will not be getting any other dates.” Later when I talk to my guy friend about this final text, he berates me and says I should have just told him the truth so at least he can learn from his mistakes. I do agree, but water has already passed under the bridge. So I hope he learns it from his subsequent dates.
Lessons Learned:
Just because you date someone who makes a lot of money, it does not mean they will be generous with their money and pay for your coffee. I believe he is clueless about how to successfully date. My hypothesis, is that it will be extremely difficult to get a second date, until he starts paying for coffee and/or meals for the first and ongoing dates. The fact that he clearly states his profession, even increases the bar, as people will expect him to pick up the bill because we know he earns so much more than the average person.
Looking back, I should have texted him the final, honest feedback text…telling him that the reason I do not want to see him any further is because he did not pay for my coffee. I make a promise to be more honest with future dates, as I do want them to improve. And I do not think I would lose much, giving them honest feedback, as long as my feedback is not cruel and is helpful.
Until Next Time, LA Dating Diaries!
As you can tell, my journey through the LA dating scene has been...an experience filled with an impressive number of hilarious and sometimes cringe-worthy stories that I literally cannot make up!
But you know what? I wouldn't trade it for anything. Sure, the constant cycle of matching, messaging, and first dates can be exhausting. And let's be real, some of these guys have been real winners (I’m being sarcastic here). But through it all, I’m still learning and exploring about myself, my needs and what I truly want in a partner, and the importance of not taking life too seriously. Part of dating is just having fun not knowing how it will surprise you.
At the end of the day, dating in LA is an adventure. It's a rollercoaster of high hopes and major letdowns. But it's also an opportunity to connect with new people, step out and laugh even the most “ick” situations. And hey, if nothing else, at least I have a killer arsenal of dating horror stories to entertain my friends (and now, all of you!).
So here's to the pursuit of love in the City of Angels - may your Hinge matches be decent, your dates be delightful, and your stories be the stuff of comedy legend. Sign up for my newsletter and follow my blog if you want more stories! :D
About Elle Tran aka L. Tran
Elle thrives on being a tourist in her own city, generously sharing over 10 years of Los Angeles knowledge with fellow enthusiasts!
An enthusiastic bike-to-work cyclist, also known as a commuter, Elle has recently embraced the world of roller skating. If you have any questions about LA, drop her a line, or simply say HELLO! Meeting new people brings her immense joy. Cheers! linhdy@outlook.com
