Updates: “Looking For More” Responds (Again)

updatesIt’s time again for “Dear Wendy Updates,” a feature where people I’ve given advice to in the past let us know whether they followed the advice and how they’re doing now. Today we hear from “Looking For More,” the widow who was seeing a widower who just wanted to have sex and be friends (and date other people) while the LW was looking for more. “When I’m with him, he’s very caring and generous, so part of me says why not be happy as long as I know it will never be anything more. The other part of me wonders how did I get to be so stupid and why can’t I just walk away?”

She updated us once before, implying she was going to leave the man who could not stop dating another woman and commit to just her: “This is so hard for me to say goodbye though I know I have to, as it is an awful situation and ultimately I will be the loser. I’m already the loser — the sex buddy. After having a wonderful husband, how did I get here? How do I do this?”

Keep reading to see whether she did actually break up with the playboy widower.

To this date my friend and I are still together after an up-and-down relationship. I chose to hang in there while he occasionally saw the other woman, who I knew was completely wrong for him as she was looking for husband #4, and when he didn’t step up to the plate, she just stopped seeing him without any reason or notice in January. So he and I are still best friends and enjoy a loving relationship. Since I will be back in my hometown for five months where he lives I will be seeing a lot of him and we have a small trip planned soon. I’m not a fool, so I know this relationship will go no further and I expect one day he will meet someone else when I’m not around, but I’m trying not to look too far into the future and just enjoy the present. I’m a VERY young 80 years old, so why shouldn’t I enjoy loving him while I have the chance and desire?

Ok, but I’m worried about you. In your previous letters — both the original one and the update, you refer to yourself as “stupid” and “a loser” because you are this guy’s “sex buddy.” I don’t see what has changed except that the other woman left him (he didn’t even choose to leave her). You admit that he will likely eventually meet someone else when you aren’t around, so you are basically enjoying being his back-up until that happens. I mean, it’s great that you enjoy his company and are a youthful 80 with desire and love to share… but I can’t help but think you’re selling yourself short.

In your last update, you asked how you got here, after having a loving and committed husband — with “here” meaning attached to someone who isn’t interested in committing to you or even making you the number one woman in his life. You’re still at that place, and you’re there because you’re allowing and enabling it. Maybe you have made peace with that, but if there’s a part of you that is still sad or still feels stupid or like a loser, I hope you will consider cutting this guy out of your life and saving your company for someone who makes you feel like you matter most of all.


If you’re someone I’ve given advice to in the past, I’d love to hear from you, too. Email me at wendy@dearwendy.com with a link to the original post, and let me know whether you followed the advice and how you’re doing now.

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  1. LisforLeslie says:

    Having spent the last four months surrounded by 70/80 year olds there is only one thing that is going to change this guy’s mind: A health scare or health crisis. Then he’s going to want to be taken care of.

    Whether you choose to do that is on you. But I will warn you as I have seen for myself: that is grueling and thankless work. Not only that but I have seen a few second marriages where the surviving spouse (usually a woman) was left without much. The husband insisted that they move into his house, but she’s not on the deed. She gets rid of her furniture and the kids claim everything. So whatever you decide to do – know that this guy does not have your best interests at heart. He may be sweet and he may love you – but protect yourself from financial and health issues later on.

    Also – where you may be willing to nurse him – he may not be willing to do that for you. Keep your eyes open.

  2. ” I chose to hang in there while he occasionally saw the other woman, who I knew was completely wrong for him as she was looking for husband #4 and when he didn’t step up to the plate she just stopped seeing him without any reason or notice in January. ”

    Wait, maybe I missed something. Didn’t you also want more of a commitment, just like this other lady? Are you secretly hoping he will have seen you stick with him through thick and thin and eventually he will come around and be committed to you? I’m not sure he will come around, tbh…

  3. Candice Conner says:

    I see nothing wrong with getting some at 80. Life is short have fun while you are alive. But do not expect him to change.You are happy now because the other woman dumped him.But how are you gonna feel when the next woman comes along. Since he is seeing other people why don’t you see other people too. Just do not sell your house or give any of thease men money. I have seen old man con men they are out there. Keep your assets for yourself never believe a sob story. Have lots of fun while you can but be very careful.Use condoms.The STD rate for older folks like you is very high so yes always use a condom. I wish you the best and much happiness.

  4. Dear Wendy,
    I read your latest reply and I think I have not portrayed Jon in the best manner. First of all he is definitely not the playboy type. More and LL Bean man. He is not looking for my money as I don’t have much and he’s financially independent . He married young to an older woman with 3 year old twins who he adopted. When she died he gave them a sum of her money for the past five years. He didn’t have to because he was the beneficiary but he felt it was right. I’m a a very secure independent woman and don’t feel like a loser and feel I’m pretty intelligent. The thing I did wrong was stay with him in the first place when another woman came into his life. Neither one of us could seem to leave the other. Then my heart became involved so when you think with your heart and not your head you make mistakes. Our relationship is not based on sex. He facetimes me twice a day. While I would love to spend the rest of my life with him I am very realistic. I am 80 and he’s 71. The problem with me is I am physically and emotionally the age of 65. No one ever believes I’m 80. It is almost too old to find a guy to love and respect you. So this summer we will spend lots of fun times together. I’ve told him it’s either Match.com or me as if another lady comes into the picture I am gone and this time I mean it because I won’t spend another summer sharing him with someone else. I learned a lot about myself the past year. For five months I went out with another widower introduced by a friend. It was close but not romantic. We went to plays, dinner watched football and movies. Talked about visiting him this summer in Maine. Helped him redecorate his bedroom. It was not an intimate relationship but a warm and close one. I could see myself being able to detach fromJon as our relationship grew. Well in March on a Monday night we went to dinner. On Friday he was texting me that there was another lady in his life and he was a one woman man. I never saw it coming. I didn’t even know he was dating someone else. It was extremely hurtful. So if I stay with Jon I feel I know where I stand and he doesn’t keep anything from me. So I guess you can’t judge unless you know the whole picture and walk in their shoes. Right now I’m happy, who knows when it will end but there’s a song I love by Garth Brooks called The Dance. Listen to it…as the lyrics go. I might have missed the pain but I’d have had to miss the dance. Thanks for listening.


    1. Avatar photo Dear Wendy says:

      I wasn’t judging; YOU were the one who said you felt stupid and like a loser. I was simply reminding you that you said that in both of your previous letters to me. If that has changed, great! Have fun!

    2. I know that song, but look, you already HAD that dance with Jon and you learned how it ended: With him seeing another woman and you feeling like crap and wanting more and yet sticking around. And now you’re starting that same dance all over again and setting yourself up for the same pain. He probably WILL start seeing another woman. He has no reason to think you’d make good on your ultimatum to leave, and honestly it sounds like he’s willing to risk it anyway. You touched the hot stove and it sucked. Why are you putting your hand back on that burner knowing it could come flaring up high at any time??

      1. Yes Kate I do realize Jon could start a new relationship someday He has said he’s not looking for trouble and I believe that over the summer he will mean that. But when I leave for Florida in the fall I’m sure he will be looking. Right now our relationship is very stable but I did learn last year that it sucks to be with a man who also sees another woman. I have vowed I will not make that mistake twice so when the time comes we will be done. I have known him as a friend for 10 years and was good friends with his wife before she passed so it makes it very difficult to walk away from that. And the funny part is the whole time I knew him I was not the least bit attracted to him. Life is strange.

      2. I know life is strange. However, I don’t get why you’re asking for monogamy from a guy who doesn’t do monogamy. And telling yourself he won’t start up a relationship when you’re around even though he did last time. It seems like you’re doing some magical thinking, trying to convince yourself you’re ok with this as long as it’s only when you’re in Florida, and that he gets it and will comply with that.

        But be honest with yourself, how are you going to feel if you find out in 2 months that he’s seeing someone else? Will you really be done, or will you start another cycle of waiting and feeling awful? I would guess the latter. He hasn’t made you any promises, so I think you need to prepare yourself that it’s not going to go the way you’re hoping against hope that it’s going to go, and your dream summer could be ruined. If you can’t be ok with being just one “friend” that he sees, you shouldn’t be seeing him. The alternative might be some temporary loneliness, but that’s surely better than feeling stupid and hurt and like a loser.

    3. Also, I live in New England, and I know that a guy who wears flannel and rubber boots can still be a shady fuckboy. Even Mr. Super Nice Guy from the Canadian Maritimes, decked out in foul weather gear and plaid, can be a chronic cheater.

      1. Totally off topic – I’m about to start a big campaign in New England. Mostly in Connecticut but also Massachusetts and New York. I’ve been working with these guys out of Boston and I seriously don’t understand half of what they say to me lol. Such a strong accent! But they’re probably laughing at me for saying “eh” so it’s all good.

      2. Ha! I felt like that with people from New Brunswick.

        I don’t have that Boston accent because I’m from New Hampshire originally, but I can do it really well.

      3. The only people I know from New Brunswick are very French, so they’ve got that weird French Canadian accent.

      4. All right, so I do have the accent a little bit. My husband does not (from CT), but he says I might.

  5. TheGirlinME says:

    @ MissD & Kate.. wait until you hear Downeast Maine.. That’s something else entirely.

    1. I’ve heard it! I love accents. Rhode Island has a really weird one. Not New York, not Boston…

      MissD, this guy wasn’t French (although he did speak French as a second language). But his Canadian accent was soooo thick, way stronger than what I’ve heard from clients out of say Toronto. There’s a subtle accent there too, but this was like another country!

      1. East Coasters definitely sound different. In Canada it’s pretty common that we make fun of people from Newfoundland. I also had a friend who moved away in middle school to rural Saskatchewan. When she moved back as an adult, she had a full-on Minnesota accent! Now that I’m spending so much time in the UK, I’m the one with the accent. Haha.

  6. Kate, there is no point in debating this with you. I know he is not dating anyone else this summer. And last year he was very open and honest with me that he was seeing someone else. That happened in the winter when I was in Florida and he told me. It was my own doing that I chose to keep seeing him when I came home. Should I have just left him…yes. I had happy days and stressful days. I promised myself I would never feel that way again and I won’t. If by chance someone comes along this summer and he starts seeing her I am positively done. If someone comes along after I go back to Florida I’m positively done. I made peace with myself last fall and promised I would never be the other woman again, I will never allow myself to be in that stressful position again. You can believe me or not. Right now he makes me happy so until that stops I’m staying. It was more me than him. I knew what was happening and he didn’t force me to stay. As I previously said we have been friends for 10 years and love each other…however we are not in love.

    1. I believe you, it just seems that you’re setting yourself up for inevitable pain. It sounds like he’ll be honest with you though – if you ask, at least – which is something.

      That’s interesting that you love each other (as friends I guess) but aren’t in love… With that in mind, and given that you’re apart for several months of the year, what’s your objection to not being monogamous?

      1. Kate. To be honest before we became intimate I only cared for him as a friend. There is a big age difference. He is 71 I am 80. I always said I’m too old for him. I am 80 and look 60, not my words. When we first got together a year ago I was starry eyed..I thought it might be the start of something nice, maybe not for forever but for a summer. Then of course the other woman showed up. It was painful if I’m being truthful and while there is not another serious woman in his life I will be hurt because I care too much. And I can’t really blame him because he’s lonely too and when I’m in Florida I don’t expect him to be alone. Complicated. Thanks for listening it helps to talk about it. I had hoped I would meet someone else who would only love me but that’s never going to happen. I’m just a young soul but 80, no man in good shape wants me when they find out how old I am. So easier to be with him as he’s fun and kind and nice to me and we have passion for one another.

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