10 Embarrassing Dating Mistakes I’ve Made So Far


1. Dating within a group of friends — HUGE MISTAKE! The ocean is massive there is no need to fish within one quadrant of the sea. I can testify to this. I dated 4 friends over a period of time, tore apart some friendships unwittingly and only realized my mistake a few years down the road. Guys will be guys and at the end of it all, you’ll realize you were the only fool in that situation. Unless you want to go around being called a car that may contain multiple passengers “The PBJ,” like I was, just stay clear of dating situations like this.

2. Dating brothers, twice — Yeah dating within a group of friends is bad enough but dating within a family? Let’s just say you don’t want to go there. Friends can fall apart and they are not obliged to see each other again but brothers don’t have that option. This isn’t an episode of Vampire Diaries where you can flit unwittingly between the Salvatores. If you can’t have them both then I’d say just clear yourself of the home-wrecker name and make a run for it!

3. Dating someone just like you — A little narcissistic I have to admit but sometimes we happen to fall for someone who is the male version of ourselves. This will not go well regardless of that honeymoon period where you’re doing everything in sync- it’s going to come crashing down faster than you realize. The very little things you dislike about yourself will become amplified until you explode. No one needs two overachievers or two OCD characters. I never really believed the term “opposites attract,” until I fell victim to this.

4. Running back to the ex who wronged you — Girls have a habit of doing this. Being a girl myself I don’t even understand it but sometimes we are so blinded by stupidity that we end up running right back to our ex’s. Don’t ever do this, there is a reason that the relationship didn’t work out and there’s a huge chance it’s still not going to work so whenever you feel like running back to the person who treated you like crap, get one of your someone to steal your phone and put you on lockdown cause girlfriend *snaps fingers* you are not going down that road again!

5. Dating an erratic Bible Thumper — And yes it’s a real thing. Being religious is not a bad thing. I love and appreciate all religions with an open mind but when someone is trying to force a religious down your throat or worse yet, make you feel inferior or insignificant for not being from their clan, then it’s cause for alarm. No one should EVER make you feel less of yourself for not conforming to their beliefs. The very idea of religion should mean freedom and expression and love but when you are being subtly condemned or judged by your significant other; it’s time to move on. I once dated a guy who made me feel like crap and blamed me for “tempting,” him and “making him,” disrespect his body if we engaged in any sort of hanky-panky. I ran for the hills!

6. Flirting or dating your best friends ex or current boyfriend — I always said I would never go down that road and always judged everyone who did that until one day the roles were reversed and I ended up being that girl. It was one of the biggest mistakes I made and I will always regret it. I didn’t actually date the guy but I admit that I flirted with him and when the situation came to light, I was mortified and ashamed because

That was a boundary I should never have crossed.

My friendship was worth SO much more than any guy

I should have warned my friend about her boyfriend when I saw firsthand that he was flirting but instead being ashamed of my mistake I left her in the dark

The trust that your friendship was built on will be irreparably broken

So the next time you think about flirting or even making a motion towards your friend’s boyfriend or ex, just walk away. It sure as hell isn’t worth it.

7. Dating for convenience — This sounds like a weird one but it’s true. Don’t ever date for convenience and by convenience I mean don’t date a guy just because he’s the only attractive guy in your class and you don’t want to spend the rest of your years alone. I once dated a guy at a camp I went to because I just wanted someone to pass the time with and he was the only one available. You’re selling yourself short, settling and wasting your time. Don’t ever think that you need to be with someone.

8. The infamous LDR —Don’t worry, I’m not going to condemn long distance relationships or take away hope from any couple dangling from two sides of the world. I just know it doesn’t work for me. It was my first year of college, he was far away and I was starting a whole new life that he didn’t quite understand and things went from good to bad in a matter of months. I personally won’t get into a LDR- you have to want it badly enough to commit 100% to the person. For me, I was barely in my twenties and I just figured there was more to life than waiting around especially since we were together for <1year.

9. Dating someone to spite someone else — Whoaa! Bitch mode alert! I have to admit I did this once. There was this girl who wouldn’t stop spreading rumors about me and saying horrid things about me from day 1. I later found out it was because her boyfriend thought I was cute so naturally, I decided to half-way date half-way flirt with her boyfriend to get back at her. Years later I realize how stupid and childish I was. I resent myself for hurting her feelings by taking advantage of the situation. Don’t meddle with someone else’s relationship because you sure as hell won’t like it if someone did it to you.

10. Dating someone to fit in – Yikes! The infamous set-up! I once dated a guy because he was friends with all of my girlfriends’ current boyfriends. (Did that even make sense?) Anyway, I dated him because of course I felt the pressure of being the only one without a guy whenever we hung out so I just decided what the hell right? And before I knew it, I was dating a guy just to fit in. It just felt like the easiest thing to do at the moment because I wouldn’t have to bring a whole new guy to the circle; I’d just date someone they all knew. Yeah, that didn’t go well. Never be ashamed of being the only one without a boyfriend. Just keep calm and SOLO!

We’ve all done stupid things, some more than others. Judge me if you want but I’m here to share my experiences. Yes I am ashamed of the mistakes I’ve made but I’m not ashamed of the lessons that I’ve learned and the person that I am today.

featured image – Instagram / Paris James