It’s Hard To Stay Optimistic When All The Guys I Meet End Up Disappointing Me

I’m dangerously close to giving up on love. I have high but reasonable expectations of guys and I always think I’m choosing more wisely but in the end, I seem to only end up with the same old problems. Here’s why I think I’m having so much trouble discerning between the good and the bad:

  1. I’m eternally optimistic. Despite the fact that yes, I’m rather jaded and cynical at this point, I still hold out hope that my unicorn is out there. I don’t know where this fountain of hope comes from, considering all my failed attempts to find him. I always think, if I just try one more time… but as long as I pick the same guys, there’s no point.
  2. I search for the good in people. I want to find the right person so badly that I look for all his positives, sometimes at the risk of not seeing the rest. I want to be more accepting and patient, so I try to focus on the good. Sometimes that simply isn’t enough and everything crashes and burns because of my lack of foresight.
  3. I overlook red flags. I will say that I’m getting better at noticing them, especially if they’re glaring, but I still have to fight my tendency to pretend they aren’t there. I tell myself, well, he’s good looking and he’s nice and he has so many other great qualities… but the bottom line is that a red flag is a red flag and there’s no getting around it.
  4. Some guys are great at hiding their red flags. I try to give myself some credit because honestly, there are a lot of great actors out there. They present themselves in the best light possible, only to let their true selves sneak out later on. This is especially frustrating because I really believe for a while that I’ve finally chosen well! Then I find out that they’re just as toxic, and insecure as the rest.
  5. The men I think are different talk a really good game. They pride themselves on their honesty and straightforwardness. Of course, I find this appealing and refreshing because I’m not into games. I come to find out they are still playing games after all because they don’t want me to see any of their vulnerability and insecurity in the beginning. I get that, but there’s no point pretending to be someone you aren’t, either.
  6. I always try to see the best in a person. I’ve not always been this way. I used to be really bitter and negative and judgmental. I’ve changed a lot but the one realm I still struggle in is the realm of dating. I have a very hard time not feeling cynical and discouraged, so I guess I go too far the other direction and try to see good where maybe there isn’t any. This means I end up making the same mistakes.
  7. I know that everyone has flaws, so sometimes I don’t see which are non-negotiable. I do have things I won’t stand for, such as misogyny, addiction issues, and bigotry. It’s the little gray areas that cause me the most trouble. I want someone who’s emotionally sensitive, for example, but end up mistaking insecurity for sensitivity. I want to accept a guy as he is, but what if that means he’s incapable of having a relationship?
  8. I have a strong personality and even when a guy says he likes that, he can’t handle it. I’m so tired of men telling me I’m intimidating. I’m intimidating because I don’t put up with any BS? If a guy thinks that’s scary, what does that say about him? No, I’m not a pushover, but that should be attractive. Even when I think I’ve met a guy who supposedly thinks it’s awesome, he feels differently later.
  9. Every man who swears he wants to be with me ends up letting me down. It sucks. It’s like men love the idea of me—a strong, independent, intelligent and complicated woman— but then they don’t have any staying power. They’re great in the beginning and say and do a lot of nice things, but all too soon they show themselves to be the same as all the rest. What am I doing wrong?
  10. They seem different on the surface and end up being the same underneath. It doesn’t matter how different they seem to be—apparently I’m secretly attracted to dysfunction and I can find it inside someone even when I don’t consciously realize it’s there. Great quality, eh? I’ll be so happy to have finally made a better dating choice only to have the same root issues I’ve had with all the other guys.
  11. I can’t help the kind of person I attract and like, no matter how I try to change. I thought when I changed as a person, I would be attracted to different men. That doesn’t seem to be the case. I’ve become such a different person but I still attract men who can’t give me what I need. I look for the warning signs and end up missing them. I thought I had built up my confidence but I’m selling myself short just like always.
  12. I can find all kinds of compatibility with a man and it’s still not enough. I don’t know what I have to do. I look for very specific things now and make sure that a guy and I have tons in common before I will even hang out with him. Even when we have that, and a spark, it doesn’t end up working. I don’t know if they pretend to have common interests with me in order to impress me or what, but it’s dumb. I’m going to figure it out eventually and we’ll both have wasted our time.
A former actress who has always loved the art of the written word, Amy is excited to be here sharing her stories! She just completed her first novel, and is also a contributor for Elite Daily, Dirty & Thirty, and Thought Catalog. Amy is the founder of What If Journey and can be found on Twitter @amyhorton18. You can also visit her website at