It’s that time of the month! I share my personal dating stories (and sometimes those of my friends)! Some are awful, some are funny, but I hope you enjoy them all. This month I’ve found myself being a little bit of a voyeur- several times on Twitter there have been threads of people sharing their bad date stories, and I’m captivated by them all. Maybe it’s commraderie or the part of me that just loves a good (bad) story, I can lose hours just by scrolling through these threads and reading about all the bad dates! So this month, I’ve rounded up some of my faves (they either reminded me of bad dates of my own, or made me cringe or laugh!) Some one prompted us: what was your most awkward date? These are my faves!
I don’t think you can out awkward a Neo-Nazi. But people tried!
I hope she chose her mom!
Famous people have bad dates too? Always trust your gut?
This has happened to me too. Are these men color blind? Surely you would notice that you have someone’s eye color wrong.
My take away? He seems lovely. She seems……not.
These both made me cringe for various reasons:
And if I noticed this it would creep me out:
Lastly, this is the best kind of awkward date and what I aspire to be:
I would love to know: what is the most awkward date you’ve been on? How did you handle it?
Have a dating horror story you’d love to share? Email me at racheladelicia@investmentpiece.com and let’s chat about featuring you on ex-files!
Xo RA
In my attempt to not only be Carrie Bradshaw, but entertain us all with the horror stories that can make up single life it’s Ex Files! Every month you get a look at some (real) bad dates that I have endured, and lived to tell the tale. Names and some facts have been changed to protect people, but I own the stories!
But this month I give you: The One that HATED His Mom. Also fun fact? Usually I do protect people a bit- changing of names and some details. This one? I truly don’t remember his name (literally so many other details were THAT shocking) and these details can’t be changed. Another fun fact? I truly believe how a man speaks about other women in his life may be how he eventually treats you–obviously there are exceptions. BUT. This one??? (insert the grimace emoji)
We’ll just call him Bob. Sorry to all the great Bobs out there.
Bob and I met at a party my ex-roommate and his new girlfriend were throwing (side note: friend break-ups can be worse than romantic breakups and my ex roomie and I were proof positive of that!). I will admit I was a bit hesitant at this party (see friend break up) but was originally charmed by Bob– he was friendly and polite and willing to talk to me when I was clearly the odd (wo)man out. He then extended an invitation to dinner. I happily accepted- little did I know that it was going to be one of those dates that made me shudder at the memory.
Bob and I met at a nice restaurant. He was again polite, holding doors, ordering drinks, all the things we are taught to look for. Conversation was easy- until we came to family background and schools. Like me, his parents had divorced when he was young. And yes- I know we can all have BIG feelings about that. However, what I was not prepared for was Bob going off for over 45 mins about how awful his mom was. Did she treat him badly? No. Awful in the divorce? No. Bob just thought that his mom was dumb, below his station in life, an embarrassment for not being what he wanted- and the kicker- he explained to me for a good 15 mins that the only reason Bob’s dad even talked to his mom was that his mom was hot. Bob really said aloud more than once that the only redeeming quality (truly to this day remembering how he called her dumb with no concrete examples and how his base belief was that women are worthless till proven other wise) was that Bob’s mom was hot when she was young. to be fair, he also said horrific things about his sister not being on his level and being embarrassing for “not being as smart as he was”.
It was very clear that Bob, on a base level, just didn’t like women. Even those he “loved”. Unsurprisingly, I tried to make the most graceful, earliest exit I could. A man who hates his mom for no reason I believe will never really love you. When Bob asked me when he could see me again I was very vague- again, he told me how smart he was, and oh so much smarter than women, so I assumed he would get it. To my surprise he called me the next day- letting me know he bought a stick shift car and wanted me to teach him how to drive it (yes, my driving stick shift came up in our date. He didn’t know how to drive it. Yet, he also mentioned he could never learn anything from a woman). I said no as quickly as I could. That was the last I heard from Bob.
Occasionally, I still think about how much he HATED his mom- in words I can’t say here the venom- for a woman who from all accounts just simply was pretty and kind and married a man with more money than she- was such a turn off. And I was so proud of me to recognize the red flags right away.
I know, I know each situation is different- but what do you think of a man who HATES his mom? Do you think it’s a red flag? I would love to hear your thoughts!
In my attempt to not only be Carrie Bradshaw, but entertain us all with the horror stories that can make up single life it’s Ex Files! Every month you get a look at some (real) bad dates that I have endured, and lived to tell the tale. Names and some facts have been changed to protect people, but I own the stories!
But this month I give you: The One who was VERY IMPORTANT
Some dates end up being horror stories because of the behavior after the date. Some dates are horror stories because of the behavior on the date. This story that combines both types of horrors. And while I maybe should have seen it coming, I was fooled into thinking it could be a great date. The issue? The way to my heart is my shoes. That can’t be a surprise. So when I met George at the supermarket and he complimented my shoes, I couldn’t see anything else. (And they were amazing shoes.)
After flirting and waiting for our juices together in line, I had learned that George was a doctor and a lover of the outdoors. We made plans to get brunch and go paddle boarding on Saturday. I was excited, I was slightly new to town, a fan of paddle boarding, and a man who sees my shoes always seems like a great idea.
Maybe I should wait to see if men can see more than my shoes?
The Saturday George and I were set to meet I prepared-my hair was cute, I was excited. He was over an hour late.
Mind you, he did call and let me know he was having car problems. At first, he thought he would only be 10 mins late. Then it was 30. Then he let me know that I should go ahead and eat without him, that we would meet up for paddle boarding. So I did.
George finally arrived, not prepared, and nonplussed that he was so very late. We headed over to his apartment (across the street) so he could change into his board shorts and we could get to the water.
While I understand car issues, and everyone is late now again, my biggest disappointment was that the charming man I’d met at the grocery store didn’t show up. This George was annoyed at every little thing, from my hair to the traffic, but as we chatted about the plan for the afternoon I discovered that George was most annoyed with my not making him the sole focus of my day.
When I had made plans with George, I thought I was clear that I was free all Saturday till about 3:30 or 4, as I was having dinner with my Grandma. George has orginally thought that was sweet. However, after being so late, George no longer thought the fact that I couldn’t devote my entire day to him was sweet. He was upset that he “wouldn’t have as much time on the water as he wanted”. And he was most upset as “he had a friend going out on a boat, there were going to be hot girls there, and he wanted us to join, but we wouldn’t be done in time”.
Yes, he legit complained that he was going to miss out on hot girls on a boat. And I let George know that if he really wanted to go on the boat that he should, there would be no hard feelings from me. He didn’t leave, but was very upset that he was missing out. I should have left then, but I didn’t.
We went paddle boarding and it wasn’t bad. I did get yelled at for not “being as good” as George was. And George did let me know more than once that he was upset that my bikini wasn’t skimpy, and that I had a time limit. But the date wasn’t the worst ever. I had no intention of a second date, but still.
George and I finished paddle boarding and I made it to dinner with Grandma on time. A few days after, I received a text from George inquiring about a second date. But, he had a caveat.
As it turns out, George let me know that he is VERY IMPORTANT and when he makes plans with someone, he expects them to respect his time and be free for the whole day. He let me know that if I couldn’t commit to that, we shouldn’t go out again.
We didn’t go out again.
Also, if you’re so important that you need people to clear their schedules for you, maybe that’s something you should pay for?
Wishing us all a week of being important and amazing shoes! And great dates!
XO RA
It’s that time of the month when I attempt to be Carrie Bradshaw, aka my own personal dating horror stories. If this speaks to you (or you just love the drama!) you can search ex files over in the search box for more, or may I suggest The BreakUp Text, Dudes and Nudes, The One Who Got Married. This month is a doozy- and sadly I didn’t break up with the dude over this (in my defense I was 23), but without further ado may I present The One Who Lied About a Party. Got Dating Horror Stories? I would love to hear them! Maybe we can even chat about you being featured! Xoxo RA
The One Who Lied About a Party
The kicker? It was my one of my dearest friend’s birthday party.
So Charles and I started dating in the usual way that you do in your 20s. We met at a party and he was cute, I was cute, there was flirting, which lead to a first date, to where we were spending almost every day together. Then (not related to this story) I broke my foot. Our dates went from on the town to more order in and be each other’s entertainment. Maybe it was a lot for a new relationship. Or maybe Charles just didn’t like it.
Either way, in the midst of all this one of my dearest friends was throwing her birthday party. There was no way that I could make it between the cast and the drugs and the pain and at the time Uber,etc, was not a thing. And ironically my “boyfriend” Charles told me that he didn’t want to go. Luckily my friend was incredibly understanding- she said it was mainly going to be her work peers, and was done around her work schedule (aka a bar by her work, later than usual, etc). As I was so put out by injury, I thought nothing of not going, was grateful for my friend’s understanding, and was aok with my boyfriend not wanting to go.
Then. The morning after my friend’s party she called me to let me know that Charles did in fact come. My friend asked him about why he didn’t come with me, and he let her know that as he and I weren’t “official” he didn’t want to come with a girl to ruin his chances with anyone else. I was embarrassed, horrified, and hurt. And honestly, didn’t know what to do.
Did I mention I was 23 and this was one of my first relationships?
I called Charles and confronted him. (Which BTW was super hard for me) I let him know that his actions hurt me, that he could have let me know about his feelings, and that I was disappointed in how he handled things, and most importantly he didn’t have to lie about going to my friend’s party. He hemmed and hawed and try to turn it into a way to ask me to define the relationship.
Sadly I let him get away with it. I was 23. And somehow felt guilty for being injured and not-as-fun. I even made him dinner. Shockingly, that relationship didn’t last. For many, many reasons- and yes, this was one of them.
An Update to this Ex Files? Bob recently showed back up. He “had such a great time the last time he saw me” and wanted to see me again. He was going to be in my neck of the woods and would love to grab a drink, etc- and while I meant to respond – I forgot. Completely. And once I realized I ghosted Bob (which I get is bad)- a peace came over me. Why waste time explaining no to someone who doesn’t get it? Why put yourself in that position? So:
Loves! It’s here! In my ultimate attempt to become Carrie Bradshaw, and satisfy my friends’ need to hear my awful dating stories (and sadly, there are a lot), we give you: Ex Files, dating horror stories. Yes, these stories really happened, yes, names/dates/places have been changed to protect those involved, and yes, if you wanted to be remembered well, behave better.
This post is a little hard to read, think about, or discuss. I’m not an expert, nor do I pretend to be. Should we have a conversation about toxic behavior? Yes. Are “nice guys” bad? Not necessarily, but loves, if you’re a nice guy who thinks that being nice entitles you to certain behavior from women: you’re not a nice guy. If you have been assaulted, please speak up, seek help if you need it, and do what you need to do to take care of you. And with all of these warnings, I give you:
The One Who Wouldn’t Take No
There was a man, let’s call him Bob, who was interested in me. Now, for part of our friendship I had no clue that he was interested, as we were just friends. And not close friends, but say hi to friends. Bob and I went to college together, and while we knew each other there, we were never close. As with most friendships that are casual and fleeting, the only contact we had for years was Facebook. And even that was casual. Bob was a nice, kind guy, but not for me. Beyond that, I never thought about him that way as we never went much further than pleasantries.
About a year ago, Bob and I ran into each other at some alumni events, grabbed a coffee, grabbed a drink. But again, I thought nothing of it and wasn’t interested in anything more. Bob asked me to dinner one time, supposedly to chat about work; but at the table Bob’s interest in me as something more than a friend came up. I politely let him know that I was seeing someone, and wasn’t interested in him. I thought that the matter was handled.
It wasn’t.
Over the next few months, Bob would reach out constantly via text and email. Just to chat. To try to make plans. To let me know that he was thinking about me. I was polite, engaged when necessary, but let him know repeatedly that my feelings had not changed. I truly though that Bob was harmless: he was nice, he prided himself on nice, I just thought that he was a bit awkward at dating. However, at some point Bob’s behavior began to go from “nice” to “not nice”. Bob told me repeatedly he was nice, and he was. However, Bob was under the impression that I owed him something for his niceness; that every compliment or gesture entitled Bob to something. Not only is that off putting and untrue, it made me avoid Bob.
Things came to a head when Bob asked me out, and I said no, as I already had plans. While this would have been the end of it in most circumstances, it wasn’t the end of it for Bob. As Bob felt he was owed something, he wanted to know why I told him no. Bob didn’t call or text to find out my reasoning. Bob showed up at my house, came in, and wanted me to explain to him why I couldn’t go out with him. Now, maybe you’re thinking that every one wants closure or deserves to know the truth; I have never had anyone else show up at my house after texting me to go somewhere to find out why I told them no. Yes, Bob was bigger than me. Yes, Bob brought up how he was a trained black belt. Yes, Bob showed up at my house to challenge a no he received. It was scary, and inappropriate, and he didn’t see that.
As many women do when faced with a situation that makes us uncomfortable, I tried to diffuse it. I explained that I had other plans, I placated him, I got him out of there. The worst thing that happened to me is that Bob tried to kiss me, it didn’t work. And while I had reinterated that I was not interested in a romantic relationship with Bob, he continued to ask me out for months, till he became too mad that I constantly said no.
I’m not sure that Bob gets it to this day.
Is this part of a larger convo? Sure. Do I know how to solve this problem? No. And do I know if ghosting is the answer? No.
Wishing us all a week of people who can take a no and amazing shoes!
XO RA
It’s ex-files, where we stop chatting fashion for just a minute and talk dating horror stories. An attempt to be like Carrie Bradshaw? Sure. But let’s be honest, dating horror stories are both horrifying and funny. Names may have been changed to protect identities, some details moved about. Hungry for more? Try: Tinder on an Airplane, Jumping to Conclusions, and The One Who Asked for his Money Back. There are quite a few more when you search “ex files” in the search tab!” Also if you want to be written warmly about- behave better! xo RA
This is yet another Ex Files where I am taking liberty with the word “ex”. This dude wasn’t an ex- we never went out on a date. But he was pursuing me (and I’m so grateful that younger me was annoyed enough with him to say no!) and makes for a great story…
Jeffrey and I met on a job. His position was higher than mine, but we had mutual friends on the gig, and while he was well known, he was also well liked. So when he started paying attention to me, I didn’t dissuade it. In fact, it was flattering and a bit exciting that someone who was witty and funny (and cute!), and also well thought of by my friends and co-workers, was flirting with me.
The thing? Though we were introduced many times, people used my name in front of him, and at one point I had a name tag on- Jeffrey refused to learn my name. Or perhaps, refused to use my name might be more accurate. I was wearing a red shirt? I was “red shirt gal” for the day. Black jeans? ” Hey, black jeans!” At first? A bit charming- as Jeffrey said it as if it were some private joke between us. Then. It became clear that calling me by “with what I was wearing” was both a bit to Jeffrey and a way to avoid calling me by name. Which, after a day or two- neither of which were charming.
Things -or names- came to a head when Jeffrey asked me to drinks (note-to late night drinks- another red flag!) and I asked him what my name was. He replied with what I was wearing (for the record, a low back shirt). I politely declined, not mentioning that it was a big turn off that someone I was working with – and expected me to say yet to a date!- couldn’t be bothered to learn my name.
And as it turns out- I dodged a bullet. Jeffrey, though charming and talented, was apparently living in his mother’s basement at the time and had a reputation of treating his dates horrifically poorly. Who knew that by simply wanting someone to know my name (when he should have!) that I avoided all that?
Here is to the bullet and bad dates that we dodged and the amazing shoes we got instead! XO RA
It’s ex-files, where we stop chatting fashion for just a minute and talk dating horror stories. An attempt to be like Carrie Bradshaw? Sure. But let’s be honest, dating horror stories are both horrifying and funny. Names may have been changed to protect identities, some details moved about. Hungry for more? Try: Tinder on an Airplane, Jumping to Conclusions, and The One Who Asked for his Money Back. There are quite a few more when you search “ex files” in the search tab!” Also if you want to be written warmly about- behave better! xo RA
This month’s ex files may take liberty with the word ex- as it’s not like we are exes. BUT. Let’s admit that dating is supposed to be the process of seeing who might be compatible with you for a long term relationship. Or at least at short term meet up. So when the person you’re supposed to me (or are writing about!) throw red flags as if they were confetti what do you do- other than not go??
And to be fair? This dude may not know that he was giving off red flags. And in my 20s I would have politely bit my lip, met up and hated him. Now that I’m not 22– I just said no. Here’s what happened:
Ryan and I met in an alumni club. What may be my fault: he is in real estate. My sister and I do notary on the side so when he messaged me in an alumni local group I assumed that was what he wanted to meet up about. He never mentioned drinks or dinner- it was always “meet up”. SO – I would give our availability and leave it. This went on for months.
Then. Messages got to the point where I got that he was asking me out (aka all of the sudden he mentioned he was interested in meeting me and wanted to get to know me)– and yet when I let Ryan know when I was free he was either busy or didn’t respond. After checking him out (yes- the internet works both ways thankfully!) I was pretty determined Ryan and I weren’t a match.
Then. He messaged me letting me know he was desperate to meet me. HE would do anything. I gave him some times. We made a plan. He canceled last min. As I was raised to be over accommodating I let him know that I was fee for coffee all the next morning. He texted me at 4p that day asking what my day looked like. I let him know that at this point I was in, I had given him times and hadn’t heard from him, had an early morning the next day and that it wasn’t good timing for me.
Ryan responded by throwing a fit over text. Letting me know that he wanted to me. That he didn’t understand the time frame. That he was going out (although in a different city) and I should meet up. Whining when I said no. Whining more when I mentioned that was not where I lived (think- Manhattan to Brooklyn), and whining MORE when I said I had a bed time as I had an early call time. Essentially crying and pushing back at all my boundaries.
And in my 20s- I probably would have relented. I would have said yes. And met him and have secretly been mad. Or when Ryan suggested a drink after my early call time I would have said yes and made sure I made it. Great news for me? I’m not in my 20s!! I no longer care about what random Ryan’s think- because truly- if they wanted to they would make a plan. Ask you out. Take all your notes into the plan.
Whining at me. Blaming me for “not meeting sooner”, acting like a 5 yo when someone said the slightest no? Not something I want in a partner. And perhaps the difference in my dating now is that I’m not looking for a date- I am super happy at home with my closet. To get past that, I need a partner. And if you let me know from the get go you’ll be a horrid one- why would I get past “hi”?
AKA. The older I am the less I let red flags fly. What are some of yours? What was a sign that someone was not for you?
I have LOVED sharing my dating horror stories with you the past few years. And don’t worry- there are still plenty of stories that I plan on sharing after the new year! But. I’ve been thinking. I know I’m not the only one with horror stories about dating and exes. Every month I get DMs and emails commiserating, telling me stories, laughing along! SO. I want to open up this space for anyone who wants to share. How will it work? You can write your own Ex Files (or send me the gist and I can write it up for you!), and then in our Ex Files segment I will share it!
-We can alter and protect every and any one as needed!
Interested? Have an idea about it? Reach out! I would love to hear your thoughts- and if you want- your ex files!!
In the meantime, I’m wishing us all a week of good exes and amazing shoes! XO RA
We’re back!! That’s right it’s Ex Files, dating horror stories, my final attempt to live my life a la Carrie Bradshaw. (And let’s not pretend horror only lives in fiction. Some of my ex files: The Ghosting, Tinder on an Airplane, The One Who Wouldn’t Take No, and of course The One Who Asked for his Money Back. More can be found under “Ex Files” in the search bar). And because it’s almost Halloween, and nothing’s scarier than dating gone wrong, we’re chatting about Haunting!
We all have an ex that won’t die. There’s a reason they call it “I miss you season”; every once in a while, an ex who’s been gone makes their reappearance. Then trick can be deciding if you should give them a second chance or not! Here are just a few of my stories of exes that came back to Haunt me!
What’s up, love?
Mario went on 2 dates over a few weeks. It was clear from the beginning that neither of us were really looking for anything serious. He was lovely–but there was no click. So when things fizzled out, I thought nothing of it. However, like clockwork, every 2 months I get a text. Everything from “what’s up, love?” to “I miss you”. At first, I thought these were a little sweet. But, as this trend has continued, it’s become annoying. We didn’t really have anything. And no matter what he’s coming back for, it’s not here.
The One I Haven’t Met
There’s always that group text you can’t really get out of’ mine involves people from college. And in the group, I don’t know everyone–but everyone is friend’s of someone I do, so I thought nothing of Dave began occasionally texting me outside of the group, it was mainly about our college team, and it was fun. However, over time, it was clear that he thought there was a connection above football. I gently let him know that I was seeing someone, and wasn’t interested. Dave was lovely and we went back to being “group text” friends. Yet, at least once a month I get sent a random meme/thought/suggestion we get together.
U Up?
Raise your hand if you’ve been haunted by an ex. We all have. From the “I miss you” text to the un-orginal “U Up?”, there’s always a feeling when someone is about to reappear. (Apparently the kids now call it “Zombie-ing”) These pop-ups can be pleasant, or down right scary (depending on the ex). I have a friend who has a theory, they all come back. And most of the time, she’s right.
So, I would love to know : who’s an ex that’s haunted you?
Wishing us all a haunting free week and amazing shoes! XO RA
It’s ex-files, where we stop chatting fashion for just a minute and talk dating horror stories. An attempt to be like Carrie Bradshaw? Sure. But let’s be honest, dating horror stories are both horrifying and funny. Names may have been changed to protect identities, some details moved about. Hungry for more? Try: Tinder on an Airplane, Jumping to Conclusions, and The One Who Asked for his Money Back. There are quite a few more when you search “ex files” in the search tab!” Also if you want to be written warmly about- behave better! xo RA
Without further ado I bring you: The One Who Argued About Football
We know that I love football (my feelings on football are ever fluid, aka mainly I’m mad about some coaching changes, and as my schedule changes I can no longer prioritize football, or use it as time alone, but that’s a convo for another post). Yet, I was raised on football, know football, and do love it. And so when that is recognized- I LOVE it.
A few years ago (or more, my sense of time is so off lately!), I got a message from one of the best football coaches of all time (and the head coach of my alma mater at the time. Yes, you probably know but as I didn’t ask for his permission to use his name, we’re protecting him!) sent me a message stating “It’s nice to see someone who knows so much about football”. As you can only imagine, this message made my day, month, year, and if at one point you heard a happy yelp that might have been me!
So, you can also imagine my defeat when my boyfriend at the time, when told about the BEST message ever was blasé. In fact, I think his exact words were “It’s not a compliment”. Note- it was a compliment. And -at least to me- it was a big deal. Yet, never wanting to rock the boat, I didn’t argue at the time.
However, a few weeks (maybe months) later, a football fight happened. We rooted for different pro teams (which can work, as long as there’s respect). But. There was a call in the game that this ex and I had different views on. He said:” You need to calm down, it’s not like you get football.”
And when I tell you I was mad. When I tell you how I hated that comment. When I tell you the joy I felt when I got to say : “Oh Really?!? According to (redacted hall of fame coach) I do get football. And I think he knows more than you!”
This was not the fight that broke us up. But I won’t lie and tell you that someone I was in an relationship to essentially poo-poo my knowledge and interests didn’t influence the rest of our relationships. I don’t think that we have to agree on everything, but I do think us thinking highly of our partners- and all of their interests is key.
Has there ever been a fight that changed how you saw partner? I would LOVE to hear about it!
XO RA
