30 thoughts on “my best friend since middle school asks me out every couple of months”

  1. Your secret is just like mine. My best friend since middle school (the first day of the sixth grade, thank you) asked me out about once a month as well… until he finally gave up our Freshman year of high school. I knew I loved him but I was not ready to go there, so I dated other guys, keeping him as my best friend and confidant. It broke his heart to see me with other people, he remembers things I’ve told him that I didn’t think twice about, but he’ll bring them up and remember every word I said, because hearing those things hurt him. We finally started dating just before our senior year of high school, and have been madly in love ever since. It’s been over three years, and we plan to get married after we graduate college. The coolest thing about it is that we know everything there is to know about one another. There are no secrets and we can be as honest as we want or need to be. So I guess my secret is that I’m so grateful that he didn’t give up on me when so many times he should have- we finally started dating because I was jealous of him and another girl, and I realized what he had been feeling all along.

  2. Persistence often wins over charm in the end. In that way I think that persistence is MORE necessary than charm to be successful in dating.

  3. i understand. i really do.
    he tells me he knows he’ll hurt me and he can’t do that.
    therefore, we aren’t together.
    when he tells me he loves me, it’s unlike any other feeling i’ve ever felt.
    watching him date other girls kills me.
    but i guess i’ll always be stuck as his “best friend.”

  4. I can relate; I met a few guys several months ago and became friends with all of them. I dated one, and relied on another for insight. To this day, I trust him more than the girl best friend I’ve had for nearly four years. The one I trusted turned out to be a such a good friend to me that, in turn, I broke up with the other for him. We almost dated but I turned him down because we both lead busy lives. He’s since dated two girls (one of them currently) and I will never stop regretting the rejection I gave him. I have recently realized he’s the only guy I’ve really been in love with.
    We’re still best friends but he refuses to discuss his girlfriend with me.
    I think he knows I’m jealous.

  5. I love my best friend to death
    I am a guy
    she is a girl
    I met her when i was an ninth grader
    I am now a senior
    That was four years ago
    I kept asking her out up until a few months ago
    She means the world for me
    Everytime i asked her out she acted like i was joking with her
    She called me last year at 11:00 pm the night before my chemistry exam and i stayed up till 4 in the morning trying to cheer her up and i am always there when another asshole breaks her heart or ppl put her down when her ex slapped her across her face and made her fall and hit her head on the side of his car she called me up and i was ready to kill him for hurting her, but she wouldnt tell me where to find him.

    there is more to it

    I am just trying to say i am always there for her I am in love with her and she says she loves me but dhe wont date me and she tells me EVERYTHING she does with other guys and it hurts

    I like your story

  6. I know exactly how you feel. My best friend was in love with me while I dated the guy I thought I was going to marry. Turns out we broke up and I found out that he’d liked me for so long. We know each other inside and out and it wasn’t long before we kissed one night months later. He told me he’d liked me for so long and couldn’t believe that this actually happened. But then he changed his mind and didn’t want to lose me because we live right beside each other and he didn’t think I was over my ex. Its been almost a year now since that one night that we kissed, and for the last year that night has repeated itself many times. I’ve been away for an internship for the last 6 months and will be back in the same city as him in June. I think about him everyday and wonder if and when we will ever able to be truly together, I think we’re both scared and everyday I wish that things will work when I get back..

  7. I’ve fallen for my guy best friend. He’s a complete man-whore but doesn’t see that at all. So he flirts terribly, and gives every (normal) impression of being interested, but it kills me because i know that really he’s like that with any and every girl. And when he says he loves me it hurts so badly because i know he means it in such a different way to me…

  8. dont be afraid of screwing the friendship up!!! if you’ve been friends for so long, give it a shot and im pretty sure you’ll last ages ’cause you love each other that way. That would be so cute, like meant to be. My best friend and I also have something like that but it’s like a love/hate relationship and long distance so it doesn’t apply.
    But don’t regret if it doesn’t work, you can always try it again later in your lives, right?

  9. My best friend declared his love for me every few years ever since I was 12. At age 23, I finally realized I loved him, too. We’ve been married a year and a half and I couldn’t be happier!

  10. Yeah this makes absolutely no sense to me. It sounds like you’re making yourself suffer without reason. I dated my best friend from 5th grade and we’ve been together well over 2 years now with plans to get engaged. Why don’t people see that it can work out if they just try? You already kiss… you’re obviously not just friends any longer… what’s holding you back? (Other than the “boyfriend/girlfriend” title).

  11. Lillian – your story gives me a bit of hope, or at least made me smile! That’s so great, thank you for sharing 🙂

  12. I’m not sure if I’m her best friend,
    But she is mine.

    Funny, she knows that I’m in love with her, but she thinks I’m not the one for her.

    And it tears me up inside, even though I’m trying to pretend that it’s all okay.

    We talk about almost everything, and before this whenever I see her I used to have butterflies in my stomach, now there are just like spears through my heart, and she told me nothing I do can change the way she sees me, as just a friend.

  13. Imagine the roles reversed I’m the girl and hes the guy. He always checks the girls he is dating with me. He tells me how he wishes he could find a girl just like me, who looks like me and smells like me. Then why won’t he just settle for me?

  14. i turned him down & i turned him down, for years.
    i was devastated when i found out another woman is having his baby.

  15. Please don’t wind up like me… twenty years later and two separate marriages with families, and we’ve just found each other again, and realized what horrible mistakes we made always putting each other off.

  16. i am you, felix. these folks telling you that you are being used, they don’t realize that the pain of not having “her” is greater (in all senses of the word) than the joy of having anyone else.

  17. she sounds like a bitch. if she cared, she wouldnt hurt u that much and rub it in your face that shes fuckking other people. fnd a nice fish, there are plenty in the sea

  18. I totally know how this feels. I’ve had this best friend for a couple of years now and we know each other better than anyone else, like totally comfortable being ourselves with each other and we talk about everything. For a long time, I thought I was completely content with being just friends and avoided any possibility of being more than that, then I realized how important he is to me. And even though we know now that we care about each other, there are so many reasons why a relationship can’t work right now, or the risk of losing our great friendship if a relationship didn’t work. It kills me.

  19. Why is this such a commen occurrence. I’m in the same situation. He stopped it before it had a chance though. I miss him more and more each day. He only says I’m sorry. That doesn’t change it though. Makes it cut a little deeper.

  20. This is my secret, but i’m the one who tried all through highschool to make him like me, but he dated other girls and kept me as a friend.

  21. wow reading this has made me realise how stupid ive been … all those years ago when i liked him i made it into something it wasnt .. i was just a little kid but now i see that there will never be anything but a friendship because it was one sided ..thank you so much for the moment of clarity …

    i just cant help that now i have once again been hurt by a boy who just wants to be friends that i do it deliberately going for a boy when i am at the age when i need a man 🙂 hmmm thank you post secret you have got me a lot to think about 🙂

  22. WHAT IS WRONG WITH YOU??? I dated a guy who never plucked up the courage to tell me how he felt. we broke up and i miss him EVERY day! if your guy had the courage you are a dumbass if you shoot him down. I’d kill for a guy who could tell me what he tels you. i relly hope you got yourself and went for it ….hop e you didn’t waste your chance at love cos you don’t know how much that hurts the person who loves you.

  23. Har-Ask him that, dont give him a chance to reply and… idunno, do something to answer the question for him. I’m in sort of a reversed role.

  24. I am dating my bestfriend from middleschool. I turned hom down for 5 years. All he ever wanted was for me to be happy, he even told his best friend that he didn’t like me so I could date him.
    He saved my life. I was in an abusive relationship and hadent talked to him in years and I called when things were the worst and he just sat on the phone with me for hours, listening to me cry.
    I am a freshman in college and know that he is the one, but like you I feel like I want to see other people. Found my soulmate too early it almost feels like. But I know that I wont get that second chance again. So keep him, your heart may wander for a moment, but it always finds its way back home

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