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Dating : How Long Was Your Longest Relationship?

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How long did your longest relationship last? Are the two of you still together? Yes? How is that going for you? No? Why not? And lastly, what do think makes a relationship works?

I asked because I have a gay friend who’s never been into a relationship and he told me once he has no plans of ever getting into one. You see, being the nosy person that I am I tried to get him to date and this was the answer I got from him. It’s just that as far as I know he never went to a romantic lunch or dinner ever, always as friends, and we go way back since college and that was over twenty years ago.

He’s an amazing person, good looking, protective, kind, and intelligent but he simply isn’t looking. He said he has no time for romance and that he wants to devote his entire life to his career and to taking care of his family and loved ones instead. Not that we who date didn’t have a career or we didn’t have a family but you get the drift. Anyway, he told me these things ten years ago and nothing has changed since. He continues to make good on his word.

He is happy with his life. Even so, I can’t help but wonder and sometimes I want to ask him, “Don’t you ever get lonely? Aren’t you going to change your mind?” But this is me, someone who is afraid to be alone, unlike him.

On the other hand, we have a college buddy who had relationships that lasted only for weeks and I could tell there was no happiness there either. As for me my longest relationship was 6 years. My shortest, well, it lasted for a month. *Laughs.*

But now I’m old enough to know that at the end of the day it isn’t really the length of time I spent with the person that is the most important. I could be together with a man all my life but what did that matter if I didn’t love him or he didn’t love me? If the two of us didn’t love each other?

Yes, time is important but remember that it all boils down to love. It is always the love that we have for each other that counts, the laughter and the happiness that we feel, and the memories we share and create together. These are the things that make a couple, a couple.

Thoughts? Please feel free to share it with us at the comment section below and don’t forget to get you Valentine’s Day gift here!


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  1. Locksley

    Well, I left my last lover, because he was/is an alcoholic’ course, left Minnesota, too. I think he stopped growing/learning, could never leave Minnie, I ‘ve been trying to leave all of my adult life, lol, it’s been 14yrs., this June 12. We’ve been off/on for 30ish years, same with some of my friends, same thing probably would have happened, funny, how your closet friends are almost like lovers (-) the sex.

  2. ME

    Longest relationship: 13 1/2 years. Lost my love to the early aids epidemic. Have no regrets of our time together. No one told me I was going to live this long, I’d have done a better job planning. Have been by myself over 20 years now. Never pursued another relationship, couldn’t have compared. Now, I’ve always been kinda a loaner, so flying solo this long hasn’t been too tough. I’ve really had a great life. My man was and is the best part of it. I got to do the exact job I wanted my entire working life. I think those two things made for a great ride! That’s my take on the subject sides.

  3. JaysSN

    2.5 years for me. That was the relationship that taught me once and for all that I’m utterly incapable of being in one, and that even on my loneliest days (a rarity, I admit) I would much rather be single.

  4. john

    My longest was about 4 minutes before he blew his load inside me. He kiss me and said thanks and went home to his wife. All the others have been less then two minutes.

  5. OVERit

    Im 42, and the longest relationship Ive been in was 6 months or so. I don’t think Ive ever understood what the gay men I find myself attracted to are looking for, and perhaps they didn’t know either. Dating for me has been one big joke. So about 6 years ago, I just stopped looking, stopped thinking about it, stopped being interested in anything other than an occasional hook up, re-focused my energies on my work and what my contribution to the planet over time would be, and I think I am MUCH happier. I have a theory about gay relationships: they resemble something that you might make out to be “nice” from afar, but upon close examination, they are mostly a HOT fucking mess. No thanks.

    • JaysSN

      That’s not a theory. That’s a pout. The theory only applies to your own relationships. And remember that the only thing those guys have in common is you.

  6. cheated_on

    Im currently in a relationship of not having enough communication. Its been 3 weeks since he sent me a message, and to let you guys know, he lives 23 miles from my home, and that isn’t even considered a long distance relationship lol. Anyways, every time I open this issue, he just says I’m being too dramatic and sometimes uses our relationship as a leverage like ” tell that to me again and I’ll break up with you”. He doesn’t remember my birthday and even our anniversary! Im very hurt but at the same time, still loves him deeply. We’ve been together for at least 2 years and 2 months. He is my first real bf and I feel like I’m gonna die if I lose him. I really don’t know what to do.

    • Jer

      Honestly . You need not put up with that…. you deserve better and him threatening to end your relationship in that manner shows what a careless uncaring prick he is
      DUMP HIS AS AND MOVE ON .. it’ll hurt possibly …you’ll be better off…trust me

  7. Christopher

    My longest was 13 yrs. I don’t really know what split us up. Well a multitude of changes had occurred. More successes for both of us. We both grew so fast in our lives that after years we found we were just going thru the motions of a relationship. I loved him and he loved me…but you don’t end it because it works so well. I tried to end it softly but in the end he had to leave me in order to handle our ending. I was single for two years and I loved it. But I did make up for not giving into temptations for 13yrs. I did indeed. I remember that time and yet I really don’t. I now look at those years as not honestly being really happy. There was plenty of sex and partying and money flowed carelessly. But at the end of the day being alone was okay. Being single wasn’t for me. So I was patient and left the door open for it to find me if it was supposed to. The one night I started chatting with a guy and we chatted for weeks being flirty and lascivious and serious. Trying to be cool and interesting on a for me (no offence) was a hook-up site. He had just dealt with a breakup after months of dating someone so we commiserated in that. I stopped chatting after awhile because with distance and schedule we found it hard to meet. But he stayed on my mind. Jump two months at a pride parade and I dropped my keys leaving a bar when this young guy kindly picked them up for me. We were amazed that in such a huge crowd and after so long we would meet there. Well he came back to my place and stayed three days. He was gone for one and then stayed for four. We dated long distance for 2 months when he moved in with me. Its been seven years. Now I am 13 years older and I had apprehensions about the age difference. Its never been an issue. I went thru all of that to find the one I was supposed to be with. I can say for me. I think single is okay but we all want someone at the end of the night to hold and hear about the day. Side note: My ex remained my best friend and became his good friend as well. He is a big part of our life. But I can say in total honesty. I loved him deeply and honestly. But it is a whisper to the hurricane of love I have for my husband. There is that one for us all. You make yourself open to the opportunity for it to find you.

  8. dave

    9 yrs. Lost my partner 1yr. ago to colon cancer. H was my best friend, my lover, and my companion. Trying to pick up the pieces. but is hard. I need to love and be loved again. I know there will never be another like him. life gets lonely, but yet i know there is someone out there for me.

  9. 52 Vs 21

    Im currently in a relationship with my bf who I met here. I got some serious tension with our relationship lately. My main concern its that we don’t communicate a lot, like the last time he sent me a message was 3 weeks ago. And one thing is, he lives 23 miles from where I am, so that’s not even a long distance relationship. He doesn’t even remember my birthday nor our anniversary. Every time I bring up the communication issues, he’d tell me that Im being dramatic and he’d use our relationship as a leverage like “tell that to me again and i’d break up with you”. We’ve been together for 2 years and 2 months. I’m suffering but at the same time, loves him so much because he’s my first. I don’t actually know what to do. Feel like I’m deteriorating every single day.

    • anonimatovato

      oh no honey, the “tell that to me again and i’d break up with you” is a giant red flag. listen to your inner voice, there replies the answer.

    • michael J.

      I do not want to disregard your feelings as they are your own! I would tread carefully sounds like he may be involved elsewhere and you deserve better than to be a mistress

  10. Mike

    17 yrs… And married 2.5… I love him dearly and he loves me. Sex isnt what it was between us… Time has made us both functionally bottoms… We’ve found our ways around that… And have bought a house and have our pets and our 3rd and are content.

  11. Michael

    24 Years and we just finally grew apart. As hard as it was at the time, I am happier now than have ever been. Wish we could have been longer but I finally deiced that I loved me more than I loved anyone else and it was time to leave. Thankfully three years later we can still chat and be friends.

  12. Michael

    My longest last 2months shy of 17 years. Daniel was the love of my life. The only reason is ended was because on 11/2/2011 Daniel passed away in his sleep at the young age of 37. It still haunts me to this day that he’s gone.

  13. JimRon

    Almost 38 years together. Live together, worked together until we retired, go everywhere together. Total opposites, not much in common, but best friends and lovers forever. We only wish happiness for each other. Murder yes, divorce no, but never go to bed with your troubles, but the bitch does not like to sleep alone. We put jealousy in a cage and not each other. We all seek the same thing in life and that is happiness. We decided all we need is someone to love, someone to love us back, enough money to live comfortably, and good health. With those we are very happy. You have to decide what makes you happy and go for it. A relationship is not easy. You really have to work hard on it and want it to work. So easy to break up and so hard to stay together, you have to fight to stay together and not fight to break up. We are a very lucky and fortunate couple to have each other, love each other, and can think of no one else we would rather be with than each other. A three way is fun once in a while to help us realize what we have with each other and how fortunate we are. Summer home up north and winter home in Fort Lauderdale. Life is good, but way too short. Most guys don’t know what they have until it is gone. My dear old Dad always told me “If the Good Lord had mad anything more pleasurable than sex, he would have kept it for himself.” Get out there and enjoy life and get all you can get, you can’t wear it out. Have fun!

  14. Steve

    20 plus years for me and mine. He died unexpectedly in his sleep. Of course it will never be the same with another man,but I am hopeful for the chance.

  15. Bill

    21 years… And then it was it was over. Things change. .. We changed He is an amazing man and i am thankful to have shared those years…. They were amazing. And so were we. We brought out the best in each other . now years later.. I enjoyed being single for a while..but the reality is he will akways be the man i love. He remarried within months and i wish them well…. But for me…. Why tempt fate? I’ve experienced and had the ideal… Why settle for something that will always be “less”

  16. William

    My first relationship lasted 15 years, my second 13. What I learned from them is that I have an unhealthy attraction to narcissistic alcoholics. I don’t know if there will ever be a third, but what I do know is that he will not be a narcissist or an alcoholic.

  17. Ron

    35 years and counting. My only relationship, his 3 (wife included). He left the wife and kids to be with me. I was content with being “on the side”. He wanted me with him so he left the married life for a gay life. I tell everyone it wasn’t easy but it’s been worth it.

    • JaysSN

      Plus, unless you die in a plane or car crash and just happen to be with your partner, you’ll die alone either way. So will all these people in relationships. Not being single at the end of life is the a fascination and goal I just can’t wrap my head around.

  18. JT

    This year will be 21 years. It’s my first relationship with a man. It has had it’s up and downs, but overall it works for us. We live 45 minutes apart, so have lots of me time to spend with friends and family. I think this is why it’s lasted so long. I need me time.

    I’m not looking for anyone else, but if we ever call it quits I don’t think I’ll get into another relationship. Basically because I don’t think there’s another guy who could take my lifestyle.

  19. Anthony

    My partner is the most awesome guy I could have ended up with after my wild years. We just celebrated 25 years of loving caring relationship. We have been married 2 years the 27th of this month. I found out I was positive a few years back and I gave him the option to leave and would always be his friend. His response was I made a commitment and I stand true to those. Even tho we don’t have sex anymore the love he gives me every day is enough. We still cuddle and our hands our always on each others when ever we are in the car and at night we always wrap ourselves in each other. 5 years ago we moved to a small town in Tennessee,he built for me my dream home. I will never find another him and look forward to growing old together. Love you Bud with all my heart!! You are definitely THE WIND BENEATH MY WINGS!!

  20. william

    In all honesty, I’ve never been in a relationship. Maybe one day i’ll be in one, but not actively seeking one. I’ve just never met a person I can tolerate to be around for more than a couple of hours at a time. True I do feel lonely at times, but I have so much I do or like to do that it rarely is an issue. I have friends that I do stuff with and if they are unavailable, I do things by myself. I must admit, I like my independence.

  21. Sean

    Mine was almost 7 years… it was better than you’d think. But at such a young age you always need to know the rest of the story before you settle down. He’s still the love of my life but maybe, just maybe separation makes the heart grow fonder.

  22. Donald Shackleford

    Mine was 11 years unfortunately people do not grow together sometimes we are still friends. He met someone a few years back nice guy I like him

  23. Del

    21 years next month and this relationship is on lock! What has made this work? Honesty, listen and understand, respect, fairness, laughter, a little pampering, must honor the relationship, continue to take each other in dates and be the best companion you can be.

  24. Steven Watts

    I am the same way as your friend.
    I have never been in a relationship either. I do go on the occasional date and hook up. But never goes anywhere from there.

    I did however try to date and take it to the next level. Random txt hey just thinking of you, weekend trips , movies, concerts, cooking a night in or out, or going on a drive..etc. But I seem to come across guys that just like hooking up and not dating.
    So since that seems to be my life. I stopped trying.
    I’ve been alone since 2005

  25. Rick

    My longest was 11 1/2 yrs, we were very happy together and we took care of my mother for the last 4 yrs of her life and the relationship, 6 months after she died, he left me due to the fact that I let looks over shadow the man I fell in love with. We are still friends

  26. apeman

    My current relationship – a little over 17 years now. There are ups and downs, passion decreases, intimacy increases. For me, the way to keep a relationship going involves among other things: compromise and accepting that his faults aren’t going to go away and neither are yours.

  27. Dan

    Like your friend, I too have never had a relationship. I call bs on him. Saying he wants to focus on his career and taking care of his family was just a way to get you to leave him alone and avoid an awkward subject for him. I mean, if he had a partner wouldn’t he take care of them like any other member of the family? It’s something I’d say to friends and I want a husband and kids.

    Being long term single is an incredibly lonely burden. I go out with friends and I feel like the odd man out. I find an attractive guy but he’s already taken so that won’t amount to anything. I even feel down going to the store and seeing couples stroll down the aisles as I throw boxes of tv dinners in my cart.

    Let’s be honest, you talk differently to people than you do your partner who you should be closer to. I’ve been dealing with a lot of personal issues lately, mostly with work and family, and I wish I had someone to come home to and talk honestly to. Instead, this past Friday I came home and took a long hot shower, tried not to feel lonely and aside from the lady at the drive thru, I haven’t spoken a word since I left work.

    It’s not for lack of trying, I’ve been looking a long time and it’s draining to put your best foot out there and not get anywhere. In my heart, I’m a hopeless romantic and I feel like one day I’ll find the guy to make it all worth it, however long or short our time may be together, but every now and then reality hits and I wonder if I’ll ever find someone to call my own.

  28. Jer

    For myself in relationships ,…my longest was three years ..that’s been 8 years ago and it hurt like hell when it ended but what can you do if someone wants to leave, but also it was when the economy tanked and we both had lost our jobs and other stuff was going on with both of us .. … made things rough, but …We didn’t part on bad terms ,but the one b4 was a almost a year he was just a coward and wanted to blame bad behavior on be a Cancer .. ( that was a year b4) and previous to him -those were many ,.. & each lasted months -if that .
    Gay men are ridiculous and have preconceived expectations , are arrogant and yet insecure about looks ,etc. and require pictures even to meet and then if you do/or say and even if the slightest things get said or done “wrong” or off . It’s over . No chance —
    ALL YOU BITCHES KNOW WHAT I SAY IS RIGHT-and that’s the fucking TRUTH !!!
    DONT DENY IT !
    But my problem has been with abused victims , for them either as children or from previous relationships…so I can’t deal with that crap . They think abuse is going to be apart of my relationship with them …so that has made me end things.

    I like having a bf . I love being in love ❤️ I’d like to marry …
    But since almost a decade now , guys seem to be,… esp locally where I live ,..not for relationships.
    & Ones that are supposedly ….that claim to be in one ……”married partnered or committed “which I find hideous they claim –
    Any of these titles
    You’re lying for one !! .. those of you of you “play” outside of your so called “relationship” which I’ve found so many it’s beyond – the one guy -the other or both .
    Sorry!
    You’re not really committed or otherwise . Look it up -Committed doesn’t include others beyond two … not for your meaningless hookups and bjs
    So, yes it’s left me to think being single has been better . I’d like to be with someone but if that’s the shit I’d have to sign on for…
    NO FUCKING THANKS !

  29. Keith

    My relationship lasted 19 years. I woke up to my partner and 2 other guys in our apartment high, and fooling around. I went into the living room and asked them to keep the noise down because I had to work that morning, and I went back to bed. I never cheated on him during all those years because I loved him. When we first met, I said to him,” if you ever become tired of being in this relationship,please let me be the first to know, instead of you cheating or someone telling me.” He then decided to no longer help pay bills which caused me to lose the apartment. He went back home to his family and left me homeless and hurt. I wanted to kill him but I realized that I had to let go of that anger and get on with my life. It was hard and still is but I forgave him and my life is better now. We are best friends now and he is there for me whenever I need him and vice versa. I love him but I’m not in love with him. He always says to me how much he really miss being with me and how much he wished be never did what he did because he now knows what he really lost. We shared 19 years together thru ups and downs, good times and bad times and that’s a bond that you just can’t throw away. Also he is that lesson I learned,” To never let anyone take my joy or power away from me ever again.”

  30. Jim

    A lot depends on luck in life. Right place, right time, happenstance of right preparation for that moment, right external features (work availability, suitably stable remuneration, etc.), all play a role in creating the environment for a relationship to develop and thrive. Then, the right guy has to be there at that time. If these things are not in place, then even wanting a relationship may not make things possible. Not expecting anything at this juncture!

  31. Rico

    Hello guys. I would like to tell folks not to give up on love. I met my prince charming 10 years ago. I was living in Charlotte NC, and he was living in Moldova, near Ukraine. We began chatting on Gay.com, and the first thing he told me was he was going to marry me and we would be together forever. I didnt believe that of course, especially since he was in another country. I just thought he was another boy trying to make some money. So I really didn’t pay him any mind, but he kept coming back everyday to talk to me. He always, kept saying he was going to move to the US to be with me. Well one day 2 months later, he came online and told me he had a plane ticket and was ready to move. I was really overwhelmed, I could barely take care of myself, more less take care of someone else. I was in such shock, it took me days to process it. During that time, he quit his job and prepared to move, while I was still processing it. On July 4th, he arrived here. We had alot of physical attraction for each other, and we ran on that for a while. Our personalities were absolutely different, and then we had to learn to deal with each other’s personality. This was not easy, and we almost split up, but begin to work through our personality issues, and then fell in love with each other. We have been in love every since, and despite all the money, immigration, and other issues that had happened early on in our relationship, we stayed united together in love. We got married June 14th, 2012, and bought our dream home last year together. I’m proud to announce that 10 yrs later, our love is much intense for each other, than the day we met. We are absolutely devoted to each other solely, extremely monogomously and loving it! He is absolutely “my knight and shining armor”. I love him dearly. So I say love can last, but you both absolutely got to give 100 to each other. It’s definitely worth it, I know!

  32. Ben

    500 years. Well, it was actually 5 but it felt like 500. Boyfriends are like boats; expensive and a lot of work. It’s more fun to ride someone else’s once in a while and save the money and work.

  33. ray

    23 years, my first male relationship , I live him to this day and always will , but I couldn’t live with an alcoholic so I left ,it took me 2 years to leave ,I always had that hope that he would see how much he changed from the alcohol .. just helped him through a bad period and broke my heart to see him as he is …I didn’t want another relationship for awhile (5 years) sadly I did fall in love with someone who was never once truthful about anything , I learned a great deal about my self and Narcciss people , I have shyed away from anything close since then
    times have changed so much and I don’t think guys are really want long term relationships at least where I live they don’t,,,gay men are fickle and quickly move on to the next dick or ass….single works best for me at this period of time, no one gets hurt

  34. Nj

    34 1/2 years. we finally got married in 2017. A lot has changed, most good, some not so, but were in it for the long haul. Hes a wonderful guy, were content. Just 2 older guys that love each other till the last breath. Kind of like our parents..

  35. Bottomchef

    10 years to the day..Drugs Sex Rock and Disco..we are still friends..30 yesrs apart..hr married a guy he doesn’t love for security..Me ..Ive had boy friends and it’s been fun.I love my own company so it’s been good .I’m open to another but, if it dosent happen I’m still Happy..


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