“I Have Months To Live. Should I Have an Affair with My First Love While I Still Can?”

“Silvia” and I first met when I was 11 and she was 19. She was my best friend’s older sister. I was a precociously bright child, and she was always kind to me, never condescending. I came from a broken home and her family sort of adopted me unofficially. By the time I was 15, I realized what an incredible woman she was. I fell madly romantically in love on top of the familial sort of bond we had. Of course, there could be no reciprocation so I kept it to myself. When I was 23, her marriage failed. I should have tried to date her then, but I just thought she was out of my league, so beautiful and sophisticated. I had nothing to offer. So I went out into the world to seek my fortune. I married unsuccessfully, divorced, drifted lost for a while. I met my second wife by chance, was married to her for many years, and raised our son with her. Then I was diagnosed with a terminal illness, given a 3-5 years expectancy at age 45. I became completely disabled at 47, and now at 50, my life expectancy is a few months.

I am still married to my second wife, and I love her as much as ever. She’s a wonderful woman who doesn’t deserve to be hurt. I’m completely honest with her and trying not to hurt her. I still love Silvia, with the same intensity and desire. It’s not something I can turn off. As I learn more about what her experiences have been, we draw closer together. We were simply made for one another. Even if she didn’t love me back, I would always love her. I would just express it in the sibling relationship terms. I never dreamed that she wanted me also. I never dreamed “WE” could be. And now it’s too late for anything but a moment. A memory. But we must fulfill our destiny. She finally said to me, “ I love you.” After 30 years of waiting, it’s the peace my soul needed. This is the truest of true love. What do you think, Wendy? — Terminal

I think that if hearing Sylvia tell you she loves you after thirty years of “waiting” – even though you never believed she’d love you back, and you never ever tried to pursue her when you were available, including after after her divorce and then after your divorce — if hearing her tell you she loves you is the peace your soul needed in your dying months, fine. Take the peace and be glad for it. But don’t pursue your “moment” or your “memory” now. Whose memory is your potential love affair with Sylvia going to be when you’re dead? It will be your wife’s who has loved you all these years and cared for you through your terminal illness and your years of being completely disabled. What about the peace her soul needs? What about the memories she deserves to help comfort her you when you’re gone?

Don’t let additional pain and grief be the legacy you leave. Let the peace you feel from Sylvia’s expressed love — in addition to the love and care you feel from your wife of all these years — be enough. Don’t give your wife more to process on top of her grief by having an affair in the very end. The narrative you’ve told yourself all this time hasn’t changed anyway: you still have no future with Sylvia. Please give your wife the time and attention you have left as the love you now feel from Sylvia brings you additional comfort in your final months.

Last year I reconnected with a man, “Mitch,” whom I had a crush on in the first grade. After 40 years, I thought it was destiny bringing us together. The problem is that he is still legally married to his wife whom he’s been separated from for over seven years, She has even been in a solid relationship with another man for over five years yet is still married to Mitch. Neither of them has taken steps to get divorced because they “already feel divorced,” but this situation is disrespectful to me and our relationship regardless of if I want to marry him or not.

Mitch shares a son with his wife, and I think deep down maybe they want to reconcile. I see no solid future with this man and know that if he can’t respect things in our relationship that I find disrespected, I should leave, right? — Mistress in San Francisco

Yes, if you don’t see a future with Mitch, and you find the lifestyle he’s led for years – even well before you started dating him — disrespectful to you and he has no interest in changing it, you should move on. You two have a difference in values and priorities, which is always enough reason to put on the brakes.

Follow along on Facebook,  and Instagram.
If you have a relationship/dating question I can help answer, you can send me your letters at wendy(AT)dearwendy.com.


  1. LW 1 – Are you really sure this is your “destiny” with Silvia? She told you that she loves you. Did she mean it in a way that says she loves you in a romantic way? If my BIL was dying of a terminal illness, I’d tell him I loved him too. I’ve never told him that before. That doesn’t mean I’m anxious to jump in the sack with him. This woman has known you for 39 years since you were a little boy. It would make absolute sense that she loves you, but it is more likely than not in a platonic way. And do you really “love” Silvia? Or is she just some woman that you idolized as a child that you’ve kept on the pedestal for most of your life? Real love is what you experience on a day to day with a real person, not fantasy about some dream woman. Do you really want your wife and son’s memories of you to be tarnished by chasing some fantasy that might not even feel the same as you and will likely not be anywhere as great as you have it hyped up in your mind to be? Sometimes the fantasy is way better than the real thing. Keep it that way.

  2. I think Silvia is not in your destiny as a lover. She is a mother figure for you, hence the everlasting love, the idealisation, and the non-realisation of any romantic relationship. You say that you come from a broken home: this makes it very obvious that this woman fills a maternal void, and also very obvious that you lean back towards that kind of attachment when you face such a prognosis. I am sorry about your illness. When we have such a long idealised love, it is not so much about the person. It reminds us the attachment we had for our parents.
    Don’t ruin it with an ill-advised sexual proposition. Really not. And yes, as Wendy said, please have some respect for your wife. Think of your legacy. This should be your worry now: what you will leave and give to your family (the real one, the one you chose and constructed).

    1. William Crowley says:

      Thank you Wendy. You pretty much said what I expected. (I find it amusing that you used the pseudonym Sylvia, as there actually is a Sylvia involved peripherally!)
      Neither you nor the readers who have commented understand the depth of the situation, which doesn’t surprise me. I do thank you for your opinions and standing for what you believe is right. I told my wife about her immediately, she knows of the emotional affair, and is aware that I am not well enough to consummate it physically. She also understands that If I were whole, I would have to go despite my love for her. We’re inextricably bound by empathy . I’m happy I don’t have to make that painful decision. I never meant to make anyone hurt or miserable. Thank you!

      1. Mate, you sound delusional. Your’s is not the deep, meaningful, super-special love of all ages – it didn’t even get past stage 0.01. Most people grow out of this narcissism once they exit adolescence. I hope your wife can forgive you for sullying her last memories and last months with you, and I hope you’re not still expecting her to wait on you after this.

      2. It’s also very telling that you express the fulfilment of this great, deep, enduring love as boiling down to physical consummation only.

  3. LW1: are you prepared to experience the absolute worst case scenario? One that not only hurts your wife, but hurts you? Because if she does not return your feelings, and lets you know, or reacts badly to your expressed interest, your last few months are going to have the additional heartbreak of rejection on top of everything.

  4. LW 1. What mediation are taking because you are not thinking clearly. You have very little time left. Try not to hurt people more than you have. Dying is no excuse. Do you want to have people think of you fondly or curse you? LW 2. What part of never date a married man did you not understand?

  5. PurpleStar says:

    My first thought was that your letter was plot synopsis for an epic love saga. The prose was there;
    precociously bright child
    out into the world to seek my fortune
    we must fulfill our destiny

    Then I read your response to the very real people of this site who have empathy and compassion for your wife and for you. You insulted them.
    “Neither you nor the readers who have commented understand the depth of the situation, which doesn’t surprise me.”

    You, sir, are an ass.
    Not the hero of an epic love story.

  6. Mrs. Danvers says:

    Well, I got a laugh out of William’s letter. Several decades ago my father, who was terminally ill and would be dead within 2.5 months after saying this, told me that he wanted to run away with one of his former girlfriends. I could understand why he was feeling that way but I also knew it was bullshit because he was terminally ill; however, I also realized it was how he was processing his life knowing he’d be dead soon. The last words he said to my stepmother was, “You were such a wonderful wife and I’m sorry that we couldn’t spend more time together.” In the end, it was who was there with him who mattered to him.

  7. Avatar photo Guy Friday says:

    Let’s accept the premise that Silvia’s “I love you” to you was sincere and in a romantic sense. The million dollar question isn’t whether she loves you; it’s whether she’d have admitted it to you if you didn’t only have months to live. I strongly believe she wouldn’t have, because there is nothing in your description of Silvia to us that leads me to believe that she would disrespect your wife like that. She told you that she loves you because she wanted you to understand that in another life, in another time, maybe something could have been pursued. But you don’t live in another life and time; you live in this one, where you are married and soon to die. And your wife loves you so much that even when you tell her to her face about how you would leave her for another woman if only you were strong enough to do so, she accepts this of you and loves you no less for it, and I’m not sure you even realize just how lucky you are to have someone who loves you so deeply and meaningfully that she would simply say “OK” and leave the matter be. You’re an incredibly lucky man . . . just not for the reasons you believe you are.

    1. William Crowley says:

      Guy Friday you are the only one who comes even close to understanding. All of this developed over the course of a year’s communication. I never had the means to find her until Facebook, and it wasn’t until I was attempting to distract myself from my suffering that I started randomly searching names I hadn’t thought of in many years. I know woulda coulda shoulda can’t come true, but wanting to hold someone I care so much about in my arms, to the exclusion of the world, does not deserve excoriation. Had I the foresight, I would never have married another. Had it been possible to find her back then, I would have lived this dream. It’s not about my wife in any way. It’s no insufficiency in her. It’s a need of mine from far before I ever knew she existed, and she would not be broken by this “affair”. I’m not asking permission or forgiveness, just seeing if anyone can appreciate what a true miracle this is. If I had fallen for some 20-something I met at the park or supermarket or whatever, that would deserve your scorn. I was looking for empathy, and I got my answer. It is still rare and precious. Thank you.

      1. Funny how the only advice that is ‘right’ is the advice you want to hear.

        Again: your poor wife. She loves you enough to be with you and care for you during these final months and you throw that at her.

      2. anonymousse says:

        I have a feeling this epic love exists solely in your mind.

      3. LW, your recent post reveals a lot. In your OG post you made it seem like this woman was very much in your life, but that’s not true. She’s someone whose name you haven’t thought about in years. You hadn’t had her contact information in years. You haven’t seen her in years. Instead of a long lost love i think you’ve been given a terrible diagnosis and you’ve started looking at your life and thinking of all the “what ifs” and paths not taken. That’s ok. You can be a little nostalgic and think of what would have been if either of you had reached out when you were single but you have to realize for what it is. An unrealistic fantasy and an alternate reality. The fact is you haven’t seen or thought of this woman in YEARS. It’s not a lost love story, if it was meant to happened it would’ve been happened a very long time ago. It wasn’t. Instead you’ve got the wife and children you have not. Focus on reality a bit after you drift into “missed opportunities fantasy”

      4. Avatar photo Guy Friday says:

        Funny how the only advice that is ‘right’ is the advice you want to hear.

        Did I give him advice he wanted to hear? I thought I was pretty clear that I thought it was purely driven by his impending death and that he doesn’t seem to grasp how lucky he is that his WIFE still loves him and stands by him despite all this. I’m not sure he even read my reply . . .

      5. Well the meaning he extrapolated from it at least.

  8. mellanthe says:

    LW, I’m sorry for your terminal diagnosis. I hope you have as much time with your loved ones as possible. It’s truly sad, and I’m sorry that you won’t get to live the life you wish you could.

    You admit that you were “randomly searching names I hadn’t thought of in many years” – it’s human, but regrettable that you decided to search up a woman you once had feelings for. But can’t you see that searching up old flames was never a constructive thing to do when you’re in a current relationship? And that it rekindled feelings that had remained buried? If you hadn’t thought about her in years, it’s not really a ‘coulda woulda shoulda’ situation – it doesn’t sound like you regretted her dropping out of your life all that much until you embarked on a passionate emotional affair (on your part)after searching her up. If it was meant to ahve been and you wanted her that badly, you’ve had an entire life to look her up and be with her.
    “Had I the foresight, I would never have married another. Had it been possible to find her back then, I would have lived this dream. ” But you couldn’t, and you didn’t. And you presumably fell in love with your wife, unless you want us to believe she’s always come second to some woman who never even gave you a scrap of indication she wanted you romantically. I’m genuinely sad for you that this is how things have turned out, if that’s the case. The point is, you made a life with your wife, and at that point you should have let sleeping dogs lie. It’s unfair to the people we choose if we dig up the past and search up old loves to see if we can rekindle them now. I don’t knwo what wedding vows meant to you, but to many they mean putting all past loves aside and chosing this person now. You had managed to get past them enough to love your wife – i hope – and build a whole life, but due to your digging up the past, you now speak of holding this woman in your arms as if you’re lovestruck teenager. But this hasn’t done you any favours. It’s awoken feelings that were almost certainly best left untouched. Terminal illness is a difficult beast to deal with, and I belive a lot of this stems from you mourning the loss of your past, and your future; it reads like a midlife crisis on steroids. There’s no need to put “affair” in quotation marks ; falling in love with a person who is not your partner, and professing a need to be with them is, in fact an affair. It’s breaking the agreement you made with said partner. It happens, and I’m not saying you should be blamed for how you feel given what’s going on in your life, but you have to own up to what you’re actually contemplating; which is breaking the agreement of your marriage and the woman you presumably promised to love and stay faithful to.

    I’m sorry I can’t see this as a miracle – you hadn’t thought about her in many years, if you hadn’t found her on facebook, you’d never have started an emotional affair and rekindled feelings. She’d have remained in the past. You might feel less alive with the intense feelings you’re struggling with, but functionally nothing much would have changed, except you might still be focusing on the wife who’s spent her life with you.

    As Guy Friday said, even if Sylvia entertained romantic feelings for you, it’s an acknowledgement of the past you shared and perhaps another timeline. Let’s not forget that there’s no actual evidence here that she loves you romantically; an old friend saying ‘i love you’ to a dying man isn’t necessarily romantic. If any of my male friends were dying, I’d tell them I loved them, too. In the strictest platonic sense; I’d want them to know that they have always meant a lot to me and would be missed. So be very careful before you read into what may never have been there.

    You can entertain the fantasy if it brings you comfort. And if you decide to pursue it, I think none of us could judge a dying man for his wish to feel loved and desired. But you may find that the reality is not like the fantasy, and you might hurt the people you’ve lovedin the process. The truth is, the person who has loved you the longest, who has shared a life with you, and who you have devoted a life to, is your wife. No passionate blast from the past can change that.

    This is special to you, but to the outside, it’s a man chasing an old intense crush who may never feel the same, to the detriment of the woman he’s loved, who has also loved him for half his life. I hope your last days are happy, but I don’t think other people are going to see things with your intensity.

  9. I’m so sorry you are dying, that must be immeasurably hard to face. It sounds like your wife loves you very much, and would do anything for you right now, dreading as she will be all the time she will be without you when you pass on. Repay her love by not making her life even harder after you have gone, –which I don’t think necessarily has to mean you must cut Silvia out; as this seems to be something which is helping you- just view her as what she has always been, a treasured family member, who you could communicate with and get comfort from like other close family, but no more. To make her fall fully in love with you, if that was to be the outcome, would be something which would break Silvia’s heart as well as your wife’s. I don’t believe you want to feel responsible for so much suffering when you leave the earth. Apart from your wife’s and Silvia’s suffering, it can only add to yours. I wish you strength and peace in the face of all you have to endure.

  10. I can’t begin to imagine the turmoil you’re going through with your illness, and please understand that I am so, so, sorry for everything you’re going through. It must be awful, first to suffer through the terminal illness, and then to suffer with this long lost love.

    Please remember something, though. No one in your situation is thinking clearly. We know in your head it’s truly a terribly romantic, tragic, almost hopeless situation, but to everyone else it’s clearly a recipe for nothing except pain for your wife.

    Please, please do the right thing. Get some therapy with someone who specializes in end of life to help you feel better.

Leave a Reply

Your email address will not be published. Required fields are marked *