5 Types of Men I've Dated, and Why They Didn't Work Out

I've dated some men. Okay, I've dated a lot of men.

And they always seem so different. I date men of all races, all ages, all religions, all professions, and yet it often seems like I am dating the same guys over and over. So I'm taking this opportunity to retrospectively categorize my past dates for hopes I can make a change. Maybe I can warn others with my past experience as well.

Puppy Love

My first mistake has always been my oldest mistake. Now raise your hands!! Especially girls!!! Who here has gone back and dated a high school ex, or their first boyfriend? I remember how in love I was with my college boyfriend. Of course he dropped me like a receiver for the Cleveland Browns. And when he found me on Facebook my heart fluttered. It was like old times!! Except now he was unemployed, had two kids, was chemically dependent and sported a spare tire. And all this could be overlooked as it didn't even touch on the real issue! The real issue is we broke up for a reason the first time. The reason, 20 years later, still existed.

The INAPPROPRIATELY Younger Man

I do think some people are wise beyond their years. Wise is derived from experiences and some younger gentlemen have experienced a lot. However, finding myself recently divorced I took it upon myself to, errr, pretend I wasn't middle aged and entertain several dates with a young man who needed me to pick him up. He asked me to bring him mushy food (almost like baby food come to think of it) after having his tonsils out. He had 6 pack abs and still ate cheesesteaks!! Yes that was incredibly hot. Yet I probably shouldn't have been shocked when I found out he had gone back to his ex girlfriend via social media. Just saying... We were a poor match. Half of his text messages were consonant letters I had to Google, utilizing sites such as urban dictionary, to translate! I hope he's doing well, but I know I can't do 20 again!!!

"We're separated...right now, anyway"

Now this one was tough. One man I met I still care for very much. But I wouldn't put my worst enemy what he put me through. After 1 year of dating and him living in his own place he told me "Well you knew I was only separated! You knew there was a chance I'd go back." Which is why I specifically asked on the first date, "is there any chance you'll ever go back?" Which of course he answered no to. But let's be fair, it was likely the magical vagina that forced him to answer no. And things do change. One putz took me out on four dates. A month later he posted a photo on the internet of him renewing vows with his "ex" wife. I feel like its a good idea to ask to see a divorce certificate at this point, just as one asks for STD test results!

I have no baggage

This is a tricky one because I've just talked about why having an ex wife is bad. But what about a man in his 40s without one, or children, or a pet turtle, or even his own casserole dish to make some food in. Didn't anyone want to snag him?? And if they did did he only attract losers? Why? Or did he just run from any and all binding commitments?? Is this really the person you want to be relying on to watch your child if you are working late? I mean he's never even had a pet turtle! And he claims he's great with kids... Hmmmm. I really liked this one guy, but I have a job and a child. Going out every night does not work. I live in NJ, not Ibiza.

The Mute

So you date all these crazy people. And its really starting to do a number on your belief in general humanity. And then you meet him. He's a finance VP of a major company. He has an ex but its official. They function well together. He's a parent and responsible and he's, gasp, NICE! When he logically asks you out date after date you say yes, because he's sweet, and you both love Chicken Tandoori and he suggests you travel together. On day three you realize all he talks about is work, and the weather and loving you. Its now that I realize, yes he's great, but it's like talking to wallpaper paste. And he's SO non-confrontational I can't even break up, because he makes excuses why we shouldn't. SMH. And because he's so calm they are logically better then my reasons for picking fights to break up.

And suddenly I realize maybe the reason I keep dating the wrong men for me is I'm not quite ready to meet the right one just yet! Lol! But so long as you remain honest, true to yourself and responsible, enjoy dating all the wrong ones!

If I'm missing any please let me know!


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What Guys Said 23

  • 2mo

    >> On day three you realize all he talks about is work, and the weather and loving you. Its now that I realize, yes he's great, but it's like talking to wallpaper paste.

    That's exactly where I'd fail on this one ¬¬

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  • 2mo

    You can think you have the right one, but I can tell you, if you're around someone else and you get so nervous and tongue tied around them. (your body feels like a panic attack) Then that should be telling you something.. yep.. happened to me

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  • 2mo

    lol. So you've run into this as well. We all have our "interesting" dates. Yes, 20 yr olds may be fun, but where is the emotional connection... what do you talk about. the've never dialed a rotary phone... lol.

    I think you are missing a big domain of emotional maturity and compatibility and that to me is the heart of the matter. From what I think I've learned, people are attracted to what is familiar in the sub conscious. It feels comfy, so they go are drawn to that. That place may not be good though and if not, thats when one needs counseling.

    Every time you date someone, stop and find out what you learned about yourself... some of that I hear above... When you suffer the most in a relationship, that is when you will grow... if you learn from it.

    That said... I have no idea how to solve this. keep dating (to get to know you and what you want and need), then figure out what you'll accept. It is much easier if you are emotionally healthy to attract someone who is. If you aren't, you'll attract someone who isn't.

    at times it seems hopeless, but I don't think it is, there must be hope...

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  • 2mo

    What about the abusive guy or the stalker or the con artist or closet gay?
    You've missed heaps

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  • 2mo

    I myself dont have any baggage, but thats because i make sure not to pick up any bad ones, plus i let things roll off my back easily. Reason Im still single? Probably because im looking for the right girl and haven't really been looking recently because i haven't really met anyone yet that blew me away even with simple things, except this homeless girl i ran into, stupid me i was so blown away by her and distracted by her beauty, even with the dirt and grim i forgot to ask her out and haven't seen her since, but if i do run into her again, i won't make that mistake twice. Plus im a romantic adventurer at heart, so im looking for my princess buttercup (princess bride reference)

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    • 2mo

      I guess financial independance isn't on your list of future mate must haves huh?

    • 2mo

      Not really, money has never been important to me, yeah its good to have it to have a place to stay and to have food and Transportation and to take care of family. Its good to have stability but other then that money isn't all its hyped up to be.

  • 2mo

    lol thats not where they failed but where YOU failed. first guy was the typical atractive but boy young girls date. as for the last one that was idiotic. you dumped a good man cause you are some sort of unthankful adrenaline junkie that feels she desrves to be entertain all the time... . idiotic creatures... .

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    • 2mo

      the only thing WRONG here is your inner self.

  • 2mo

    That will sound very familiar to a lot of people especially women in their 30s and 40s plus similarly aged men with little tweaks. Here is an extra one "I love you but I am not in love with you yet", you are the safe option and he/she is trying to convince his/herself to fall in love quite common among younger ones from troubled backgrounds. It becomes strange when they are using the physical side to keep you interested until they figure out what is going on, it is a total mess and the odds of it working out to mutual satisfaction are quite slim.

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  • 2mo

    Lol, that was awesome.

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  • 2mo

    Your never going to be happy
    I'm sorry

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  • 2mo

    You know the one constant in all this, right?

    I think that's where the problem is.

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    • 2mo

      Nah... I've had decent healthy relationships. But if you can't laugh at life you seriously DO have issues!

    • 2mo

      That's the only thing you've written that I can say I agree with.

      But it's also the only thing I read all the way through.

    • 2mo

      nuh i've had "decent healthy relationships" which you all killed. lol, so much for healthy.

  • 2mo

    In a nutshell, the five guys you have broken up with are for the following reasons:

    Guy 1: Due to some mysterious reason.

    Guy 2: He left you for his ex-girlfriend.

    Guy 3: He left your for his ex-girlfriend.

    Guy 4: Because he rolls with no string attached.

    Guy 5: Because he was unexcitingly too calm and nice.

    Hypothetically, if we dated and broke up, it'd come down to the reasons you advanced for guys 4 and 5.

    Have you ever given a thought about: what type of a girlfriend am I? Could I be responsible for some of my breakups? What about my personal circumstances contributed or caused the breakups?

    Often, breakups do not happen because partners weren't compatible, or due to age difference, personal values, and one's lifestyle.

    A recent study attribute most breakups to three main reasons:

    (1) The needs of one party (or both parties) in the relationship has evolved.
    (2) The personal circumstances of one (or both parties).
    (3) Lack of communication.

    The study concluded that why compatibility may contribute to relationship formation, it is not a reason (at least not strong enough) for breakups or why some relationships last longer.

    The said study did prove that partners who were less compatible on dimensions, such as values, interests, and lifestyle sustain longer relationship than some of their highly compatible counterparts.

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    • 2mo

      Well of course im responsible silly. In part because I've tried to make things work with people im not compatible with.

      I am not perfect. And id never say i was. But ita about finding perfect for you. Not someone perfect

    • 2mo

      well said newbie!

  • 2mo

    No one will date me because im Mexican

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  • 2mo

    " My first mistake has always been my oldest mistake " yea, that's kind of the definition of the first. The oldest one lol. Sorry to point that out, just made me laugh.

    I'm lucky enough to have avoided dating any crazy women, so no real issues past it just didn't workout. Highschool sweetheart and I broke up due to maturity issues on both ends. I liked the attention I got from other girls and maintained female friends I probably should have said goodbye too and my girlfriend at the time wouldn't come to me about things that was bothering her.

    Next girl we broke up because I wasn't over my ex and couldn't handle a new relationship emotionally and all she was doing was trying to progress our relationship further.

    College girlfriend and I broke up because I never got along with her mom and she didn't havethe stones to defend me, when her mom had something to say about me behind my back. Yet, I defended her when others spoke ill of her behind her back. I felt disrespected, so I pretty much checked out of the relationship. She wanted to go on a break, but I was done so I said let's just break up because breaks are bullshit anyways.

    Next girl was honestly marriage material, but part of our relationship ended up being long distance and the distance became too much to deal with. Literally the only reason we broke up, so of course her new boyfriend hates me. Because she chose me over him when we first started dating and the only reason we broke up was the distance. He's her consolation prize : 0.

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  • 2mo

    Fuck dating and FUCK relationships!!

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  • 2mo

    I don't think the guys you date vary very much inside despite of race, age and religion XD

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  • 2mo

    "And suddenly I realize maybe the reason I keep dating the wrong men for me is I'm not quite ready to meet the right one just yet! Lol! But so long as you remain honest, true to yourself and responsible, enjoy dating all the wrong ones!"

    This. It's not the guys toots. ;)
    95% of them out there are not gonna be the right fit. So hold out and make something valuable of yourself in the meantime, and then when you DO find the right one you'll actually have something of value to bring to the relationship. More and more today the ladies think all they need to bring is the vagina, that the guy will manage the rest of it. It's just not realistic.

    What exactly do YOU bring that is of cherished value?

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    • 2mo

      A friend once labeled me a unicorn :D Im not young, but im emotionally stable, healthy, intelligent, funny, athletic and artistic. Im sucessful career wise and have a happy, well behaved child. So i may not be your catch, but Im A catch :)

    • 2mo

      It could take 'till your child is closer to adulthood that you'll find someone more compatible. I'm not sure the percentage, but there are plenty of quality guys that just aren't willing to step someone elses kids. My second wife did it and got zero appreciation from anyone but me - but that changed around after all the kids were grown - she became their 'real mom' since the bio one was so obnoxious - even to her own kids. Very punitive and ugly. Anyway, steps have no power and frankly, most moms don't want them interfering when it comes right down to it.
      Enjoy our time with your kid - that's what they really need. And in few short years they're up and gone and you can do whatever the F you want then. :)

    • 2mo

      Steps have no power? You're an idiot. Adoptive parents are totally f***ed by your logic, along with godparents and grandparents, who could be just as biologically similar as the steparent. Oh wait, you say it's different because a biological parent is there? Doesn't matter, stepparents are there to be guardians, not biological parents. And the biological parent present HAS to trust them if they want a complete functioning family, consent of the absentee biological parent is not required, in fact, I encourage their complete absence outside of child support, even AFTER a viable guardian has been found (this course of action would not always apply depending on how relationship ended). I'd think a smart single parent would welcome this arrangement to avoid getting drained energy wise. By the time the kids are grown, their spirit, their drive, will probably have withered. All these single in their 50s who have raised their kids claiming how "happy" they are, I don't believe them.

  • 2mo

    I have one type of women the bitch selfish type

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  • 2mo
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    • 2mo

      Lol. No!! Drama was the two men in their 40s no baggage. It was always "i hate drama", with both!! Which explains why they didn't have kids... I mean lets face it. I love mine but they dont exactly creat a zen environment

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    • 2mo

      I know a "mute" who "doesn't like drama". He's married to an emotionally abusive drama queen. He hates drama so much that he won't leave her, because simply telling her how he feels would be drama that he can't just hole up in his bedroom to avoid. He's a white-knight too. He only stands up and gets mad if a child, animal, or his own immediate safety are in question, but he takes her side in any and all arguments.

    • 2mo

      @dragonfly6516 Right, that's not really me either. I have been with women who pick fights just to pick fights. That stuff ends fast, but non-confrontationally. "This was a mistake," I'll say. "I wish you well, but I probably shouldn't have called."

  • 2mo

    Hmmm... All those different men an yet one common denominator in why things didn't work.

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    • 2mo

      Yep. Post wall and still thinking the "magical vagina" can work the same charms it did at age 20.

  • 2mo

    I think you are too picky. This way, you will end up alone.

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What Girls Said 8

  • 2mo

    Jesus Christ. Did we date the same guys or something? LOL

    I have to agree with @Browneye57 though - all of these types are out there for the pickin's but it's us who keeps picking them for some reason. I finally had to take about five years off from dating and sex altogether to get comfortable with life alone before what I truly wanted came along, very unexpectedly, and later in my life. :)

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  • 2mo

    I LOVE this post.

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  • 2mo

    "The Foreign Man."
    I had Married a Muslim Man who had Found me on Facebook a few years ago. I ended up Hopping on Board and going Abroad and on my Second trip Over... We ended up Tying the Knot at the Ministry of Justice. I resided for Awhile with him and his Family.
    It didn't Work out, sad but true. With our own Personal issues in this Marriage, being Apart, and me not Going back when I said I would, Due to the Unrest that has Grown and Gotten worse, we are Now... Estranged.
    Good luck and Great question. xx

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  • 2mo

    great

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  • 2mo

    lol, but I do like your last statement about maybe you just aren't ready to date the right one! I felt the same way when I met my husband I was so ready to meet the right one and he better be it.

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  • 2mo

    Damn you have been around

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  • 2mo

    The engineer who saw "his woman" as another project to tinker with.

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    • 2mo

      Yikes, what happened there?

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    • 2mo

      Are you f***ing serious? What a dips***. Should have thrown that book and his controller at his head. Learn more in that split second than in all his hours wasted in front of that dumb thing.

    • 2mo

      Like I said, it was more about power and controlthsn anything. Some people take it too far.

  • 2mo

    Nice MyTake, I'm familiar with the first type of guys, even after high school, I still think they are cute :D

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