Red Flag Alert: Trying (and Failing) to Avoid Dating Disasters

What do a con-artist, a pedophile, an ex-gang member with a glass eye and the most popular guy in school (who also happens to be a drug addict) have in common? They’ve all dated me! Yes, I’ve certainly made some poor choices when it comes to matters of the heart. I’ve discovered that one of the biggest factors contributing to my horrid track record is the fact that I tend to either miss red flags or just straight up ignore them. Not recognizing red flags, or making excuses for them, is one of the best ways to ensure that you will end up getting hurt.

Where is the silver lining, you ask? Learning from these mistakes! If we can just take the time to recognize the flags we have missed in the past, and try to apply that knowledge to the future, we can surely avoid a few unnecessary heart-aches. Not only can we learn from our own past mistakes, we can learn from the stories of others who have ridden the roller coaster of love and got thrown off the tracks.

I shall share with you a few of the WORST mistakes I have made, along with some of the red flags that could have saved me a lot of time, heartache, money and energy.

Red Flag #1: He asks to borrow money from you.

Within a week after dating this one guy (who turned out to be a con-artist who had done hard time for fraud in the past), he began asking me to borrow money. He kept asking over and over again without having ever paid me back. What’s worse is I just kept giving him what he asked for. He had a reason for everything: “I don’t have a job yet because I just moved here from New York.” “I had to borrow money from my friend because I needed gas to look for jobs, so now I need to pay him back.” “I’ll have money coming in this weekend from my parents, I just need to get by until then.”

The list goes on. It’s one thing to borrow five bucks for parking if he doesn’t have cash on him. It’s a totally different story when he is asking for larger amounts of money and doesn’t even pay you back. Even if he has good intentions (which he most likely doesn’t), is this the kind of guy that you see yourself with? Is this guy ready for a real relationship? Probably not.

Red Flag #2: His stories don’t add up.

I once dated a guy who claimed we needn’t use condoms because he was infertile due to radiation exposure from his time overseas in the Navy. This sounds noble, right? Brownie points for his sacrifice! He later told me about his son, who was conceived AFTER he got out of the Navy. He hadn’t even realized that his two stories just completely contradicted each other. When I called him out on it, he tried to laugh the whole thing off.

Our safety is no joke! When their stories don’t add up, that is a huge flag; we must either walk away then and there, or call them out on it. After you call them out on their contradictions, it’s going to be up to you whether or not you believe their excuses.

Red Flag #3: He has a glass eye from being shot at by a rival gang.

This one is pretty bad, I’ll admit that. It’s pretty self-explanatory. The key is not to let yourself get carried away in a supposed miraculous turn around in a guy’s life. Is he a recovering addict? An ex-gang member? Whatever his story is, if the life-altering events which “turned his life around” happened recently, he probably isn’t in a stable enough position to be serious with you (even if he wants to be!).

Bad boys like the good girls, and we like them back. This road usually ends by smashing into a giant brick wall, so be ready to bail when the flags start popping up.

Red Flag #4: He breaks up with you because you won’t sleep with him.

He was my very first boyfriend, my high school sweetheart, the most popular boy in the school, and the king of the dance; he broke up with me after four months because I wouldn’t sleep with him. I had this notion that waiting until after high school was the right thing to do. Having just turned 16, I didn’t feel like I was ready. But after he broke up with me, I began questioning everything.

Was he right? Was sex what people did when they were in love? Was I being a bad girlfriend by not “meeting his needs?” Was sex totally normal for kids my age, and was I the one who was in the wrong for not having it?

I got back together with him after a week of being apart, even though I still wasn’t ready. I had sex with him; it hurt me physically and emotionally, but I kept the guy. I was sooooo STUPID!

As a 25-year-old now, of course I realize that he was the one in the wrong, not me. And our age wasn’t even that main reason for this being the case. No matter how old you are, or what position your are in life, you should never be pressured into having sex.

A relationship is about so much more than sex, and if a guy is willing to break up with you over sex, you are much better off without him. That is not the man you want to spend the rest of your life with and build a family with. So be on the look out for this, don’t let anyone guilt you or pressure into having sex!

Red Flag #5: He says “If you love me you would… (insert action here that you are opposed to doing)”:

Remember the guy who broke up with me because I wouldn’t have sex with him? Well, it shouldn’t come as a shock that a few months after we got back together and closed the deal, he started pushing for more. He wanted me to be okay with him doing drugs and drinking all the time; which I didn’t even know he was doing prior to that point in the relationship. He wanted ME to do drugs and drink with him. We had this same argument over and over again for a year and a half; him arguing that if I loved him I would do these things, me arguing that if he loved me he wouldn’t be asking me to do these things.

If there comes a point in your relationship where you’re being given ultimatums, and being told that you would do something if you really love the other person, you’ve got a giant red flag waiving itself in front of you. It might be time to jump ship and save yourself.

Red Flag #6: He is a few decades older than you, and you’re scared to say no to him.

Being scared to say no to your partner isn’t good, no matter how old the two of you are. It just so happens that in my situation, the guy that I was afraid to say no to turned out to be 45, and I was 19. Oh yeah, and it turns out he was also a registered sex offender – a pedophile. (I can see why he liked me so much!)

There are plenty of examples of successful relationships despite differences in age. If it’s right, it’s right, and you can’t help that. But if things don’t feel right, AND there is a giant age difference, it is time to clear your vision and recognize the red flag. From the very beginning, this guy that I was with was extremely intimidating. We worked in the same office and had the same friends. The first time he asked me out I didn’t even want to go, but I was afraid to say no and upset him. He claimed to be 39, and also was working under a fake name. He was also a special forces veteran, which I let cloud my vision (if he was in special forces, protecting our country, he should be a good guy.. Right?…) After a few dates and even sleeping with him twice (which I really didn’t want to do, but again I was afraid to say no), I knew I had to find a way to end the relationship.

*Break-up tip: When you are breaking up with someone who you are afraid of, be smart about it! Do it over the phone if you can. If you have to be in person, have back up ready! When I broke it off with this guy I gave my mom and a police officer friend of mine this guy’s address and phone number. I told them the exact time I would break up with him, and they both were going to call me ten minutes after that to make sure I was okay. Everything turned out okay and I didn’t need to be rescued. But I could have avoided that whole situation if I had been more cognizant of the red flags from the very beginning. His age and my gut instinct to stay away should have been enough of a reason for me to say no to the very first date.

Jen Lynn is a third-year law student from Florida, who’s had a passion for writing since she was a little girl. Jen has worked as a personal trainer, a pharmacy technician, and gone through the police academy all before the age of twenty-three. Suffice to say, she’s changed her mind a lot about what career she would like. She is hoping that being a lawyer will provide a stable income and allow her to pursue her love for writing. You can find Jen on Twitter.