Red flags are a funny thing because they are always glaringly obvious after the fact, but in the moment can feel like minor setbacks that can easily be overcome. Ha!
I talk a big game about not dating shitty dudes and paying attention to red flags and knowing your worth blah blah blah. But here’s the thing: that’s because I have seen and straight-up ignored MANY red flags over the years. I have dated a variety of shitty dudes. I am an expert in that department. It’s what I do best!
While I have (thankfully) gotten much better at spotting these dating red flags early on and not being a wimp and saying goodbye to the bullshit, it has taken me years of trial and error to get it together. And I still don’t even fully have it together! It’s really effing hard to say goodbye to someone you really like just because of one teensy little bump in the road, like them ignoring your text for two weeks or having a wife. We can still make it work!
Kidding. Kind of!
When I started recording my podcast and really reflecting on my dating past it really began to become downright hilarious how blatant the red flags in my relationships had been because wow they were CONSTANT. Every dude had some weird things going on that should have sent me running for the hills and instead kept me around for another 8-24 months. Yikes.
As of late, I’ve been pretty burnt out on dating and really can’t bring myself to do it but I thought it would be funny to take a look back at all of the straight-up ridiculous red flags I ignored throughout the years. I would say that this will help you avoid them but honestly, they’re so obvious I don’t think anyone else will have a problem!
Enjoy!
2011: THE MOST DRAMATIC RELATIONSHIP
Oh 2011, what a year. I had just graduated high school and had started college at San Francisco State University and was feeling like a true adult at the ripe old age of 17! Good times.
I briefly dated this guy I went to high school with and I can’t decide if he was incredibly toxic or just 19. They’re pretty much the same thing.
In all honesty, I feel like I should get a pass for this one because I was so young and the whole over the top, emo relationship thing seemed very exciting and how things should be. Don’t we all do dramatic weird shit while dating when we’re barely legal???
This guy was the WORST but I was so into him simply because I was desperate to keep his attention. He would ignore me for days and days, be legitimately mean to me, and break up with me constantly. He would write strange, ominous Tumblr posts and get angry with me at the drop of a hat. Plus, he made it very clear he was in love with some underage girl who was still at our high school which looking back was very creepy! He was a nightmare! 2020 Sheila would obviously not stand for this as I am in bed by 8 pm and have no time for late night text fighting.
Eventually, we broke up for good and after a day or two of sobbing in the bathroom at school, I got over it and started dating a guy 10 years older than me. Atta girl.
Red flag: treating me TERRIBLY!
Lesson learned: Normal guys aren’t rude or weird to their girlfriends. Also, don’t date anyone who still uses Tumblr
2012: WE NEVER LEFT HIS APARTMENT
The first guy I ever met through a dating app was (I think) 9 years older than me and lived in a cute little apartment in Cole Valley. I know this because for our first date I WENT TO HIS APARTMENT. Idiot!
Also, I had to call a taxi to go home LOL. Pre-lyft era man. Hilarious.
Anyway! Thankfully he did not murder me and we had a lovely time and I found him to be totally adorable. The problem? I had said on my dating profile that I was 21 when in fact, I was 18. Oops.
The level of delusion that left me believing that even after straight-up lying about my age I would end up in a relationship with this guy is truly remarkable. So I was a red flag myself!
Besides the fact that I was a liar, I didn’t notice for a very long time that he never seemed interested in us seeing each other outside of his apartment. In fact, we never once went on a proper date.
But did I think this was strange? Nope. Made perfect sense to me. Also, that way I didn’t have to pray that my fake ID wouldn’t get rejected if we went to a bar.
Eventually, I did tell him the truth about my age and not surprisingly, he was not thrilled! And finally, after I did invite him to some sort of outing and he made up 2000 excuses not to go I realized “hey wait a minute…we’ve never been outside of his apartment. That seems a little weird” YA DON’T SAY?!
Sigh. To be 18 again. Not enough money in the world, I’ll tell ya.
Red flag: never wanting to be seen in public together.
Lesson learned: don’t be a liar and also don’t go to man’s houses for a first date!!!
2013: IF HE WON’T TELL HIS MOM ABOUT YOU, IT’S A PROBLEM
I had a boyfriend for a couple of years starting when I was 19 and he was kind of the worst. I could honestly list several red flags here but we’ll just stick with a few of the most obvious.
The first is that despite being together for two years, saying that we loved each other and him meeting my parents, he still never wanted me to meet anyone in his family at all, especially his mom.
I guess I didn’t necessarily ignore this as I did bring it up to him often and told him how much it bothered me that he clearly didn’t want to fully integrate me into his life but when he would feed me some bullshit excuse about not wanting to rush things, I always fell for it.
We came from two very different cultural backgrounds and I knew that his family probably just wouldn’t approve of me but I didn’t understand why he wouldn’t just tell them to get over it if he really loved me so much. Ah and there it is. Did he really love me all that much?
I think he did but I also think he did not ever consider me as an option for a long term relationship and someone who he would ever actually marry, a fun fact he conveniently kept to himself and would jump through hoops to avoid when the topic was brought up.
Of course, meeting family is not something (at least for me) that I think should be happening right away but if you’re almost two years in and you still haven’t met anyone important to him then chances are they don’t even know you exist!
Red flag: not introducing you to family after an extended period of dating
Lesson learned: If someone is hesitant to tell their mom about you it’s NOT good
2013: NAME CALLING IS NOT FLIRTING
While we’re on this guy, let me slip in one more major red flag that would send me running for the hills if it happened now.
This boyfriend had this charming little habit of calling me awful names as a “joke”. In front of people. A lot. While it made me uncomfortable (duh), I always laughed it off because I knew he was kidding. Or did I? I just chalked it up to flirting and tried to ignore it.
He also would constantly argue with me about things like why women should be allowed to take maternity leave, why men were more valuable in the workplace and other prehistoric ideas on women and equality. So I was dating a sexist and as we got closer and closer to the end of our relationship it became a huge tension point for us.
Eventually, we broke up in the old fashioned way: he tried to fight a guy in a bar for “thrusting his penis” on me when we were standing a good 5 feet away and all this poor man did was say “happy new year!”. It was my out and I took it.
Red flag: mean creepy sexist behavior!
Lesson learned: being called a slut in front of your friends is not flirting!
2015: IF THEY CAN’T SAY HOW THEY FEEL SOBER IT PROBABLY WON’T WORK OUT
Not too soon after I broke up with my lovely ex I mentioned I above, I started dating a new guy that I actually really liked.
He was cute and very sweet and attentive. The problem was that when it came to expressing his feelings about me, he was pretty limited unless he had a beer in his hand.
He was a heavy drinker and a major lightweight (not cute) and would get totally smashed on the regular and then call me up and tell me how much he liked me and how he wanted to be with me. But then, funny enough, when I would bring it up the next day as he nursed his hangover he would have no recollection of the conversation. Interesting.
I hung onto these moments when he would share his feelings for me and used them as my reasoning to continue seeing him even when he did things like not text me back for two weeks (red flag #87) and accidentally get my car towed.
It was fitting that in the end, he broke up with me by drunk dialing me in the middle of the night and telling me that he wasn’t good enough for me and that I deserved to be with someone who had their shit together and oh also he had met someone else. So.
Dating eh? Wild stuff.
Red flag: If he can only tell you how he’s feeling when he’s drinking that he can’t be that into you
Lesson learned: Communicating your feelings should not be that hard
2015: MY BOYFRIEND WHO DIDN’T WANT TO BE MY BOYFRIEND
Oh, this one is a doozy.
I fell in love with a guy who was annoyingly handsome and sweet (at the time) and smart and seemed to me to be too good to be true when we first met (he was).
The best part was that he actually liked me as much as I liked him (this turned out to be incorrect) and I couldn’t believe someone so wonderful wanted to be with me. How lucky could I be?
If this was a movie I would haunt my younger self and yell “run! get out while you can! danger!” but alas, this is not.
The first few months of dating were great and I already knew I was falling for him. And I truly believed that he felt the same way and that any day now he would be asking me to be his girlfriend.
That day did not come.
The first time I brought up the whole “so what exactly are we doing…?” conversation he told me he wasn’t dating anyone else and didn’t want to because I was “amazing” and with that piece of knowledge, I sang in the streets and waved at complete strangers for a good three months until one day I thought…
Wait. Does that mean you’re my boyfriend? Or nah?
So I revisited the conversation and so began the many months of this stupid boy coming up with excuse after excuse of why we couldn’t be together, yet.
He was too focused on his new software engineering job. He had just gotten out of a relationship only a measly year and a half before we met. He felt like before we could really be a true couple we needed to go through something serious together, like a trip to Mexico.
I shit you not, that is something he told me once.
And as the excuses became stupider and more ridiculous I still continued to fall for him more and more. It made no sense at all but any time I would get upset about our relationship being stagnant he would do something like tell me I “felt like home” and I would swoon and not bring it up for another two months.
Eventually, in the summer his birthday rolled around and I got him this nice watch and brought him treats and was nothing but the angel that I am and for some reason, this gesture really turned things around and the next morning he said “Sheila you’re my girlfriend, you’ve always been my girlfriend. I don’t know why I’ve been so dumb” and I could not have been happier.
Unfortunately, this feeling did not last as I began to realize that things weren’t necessarily changing now that he made his declaration. He still didn’t want to meet any of my friends (we dated for a year), he still wouldn’t text me back for days, he still would constantly cancel plans. And once when I asked him if he would say he had a girlfriend if any of his coworkers asked he said: “they actually did and I said no”.
So. There’s that.
Eventually, he broke up with me a week before my birthday by telling me he wanted to take me to lunch and then pulling over on the side of the road and telling me he would never want to marry me. It was very on-brand for him.
Now looking back the whole thing is laughable but at the time I was very very very sure that he was the one and therefore was very very very upset. It just goes to show that even the things you think you’ll never get over will become things of the past someday. Good riddance!
Red flag: Never fully committing despite claiming he wasn’t seeing anyone else (yeah right)
Lesson learned: If someone actually wants to be with you they will make it very clear
2018: HE WAS MARRIED
Yes, you read that correctly. And let me clarify: he was in the middle of a divorce so I guess the correct term is separated.
I’m not sure if being separated in itself should necessarily be a red flag but I do think that unless you’re in your 40’s it’s not worth the trouble of dating someone who is still legally entangled with another person.
However, the red flag here isn’t so much that he was married, it was that he didn’t tell me he was married. I found out on my own by stumbling upon some pretty undeniable evidence in his apartment (it was an accident, I wasn’t snooping I swear!).
Then the red flags began to pile up. He still got his haircuts from his ex, despite her asking him to find someone else (ouch). One time I caught him staring at photos of her on his computer while I was there. He initially said he had filed for divorce but later revealed he hadn’t actually done that part (seems like a pretty important step in the process, no?) and kept changing his story.
And yet. I stayed.
But! This time for not too long. Less than a year. Because the other big red flag was that he was an awful lot like the ex of mine I mentioned above who had some serious commitment issues. Every time the relationship conversation would come up he would put his hand over his face dramatically, pinch his forehead, furrow his brow and tell me he just can’t make himself officially call me his girlfriend and he needed more time.
I don’t know why this reaction did not repulse me (because who wouldn’t want someone to furrow their brow anytime you mention being together?!) but for some reason, I believed him when he said he just needed time. I mean, he was going through a divorce after all (lololol I’m dumb).
So despite the fact that we agreed to date exclusively (which in my opinion, is the SAME thing as being in a relationship) and that we saw each other constantly he still could never pull the trigger.
So finally I broke up with him because after giving him one last chance (via heartfelt letter explaining how I felt about him and how much it bummed me out that he wouldn’t fully commit, I am in the 8th grade) he still couldn’t make up his mind. Thankfully this time it was only 8 months down the drain, but it still hurt for sure.
Red flag: clearly not over his ex
Lesson learned: don’t date someone who has just gotten out of a relationship (or in his case, was in the process of) because they are likely still very emotionally invested
There are WAY more juicy and truly unbelievable aspects to his story that I’ll actually be sharing in season two of my podcast, It’s Not She, It’s You. Coming very soon! And yes, he did an interview. It’s a good one.
Thanks for reading! How you enjoyed me thoroughly putting myself on blast LOL. Also, leave some ridiculous red flags you’ve ignored in the comments below so I feel better!
Xo,
She
