May/December Romance?

Hello, fellow MHers:

I’m a man who’s almost 65—but a young 65, a veteran who’s in pretty good shape. I’m widowed for nearly 10 years now.

I’m wondering if you can offer me your thoughts, pro versus con, regarding a relationship that I would hope would result in marriage. The woman is 36, so there’s a 29-year age gap. She has two young children who are really great.

So what do you think? Is a deepening relationship something I should pursue? Why or why not?

Click on a heart to thank the author of this story!

Average rating / 5. Vote count:

No votes so far! Be the first to rate this post.

We are sorry that this post was not one of your favorites!

Help us understand why.

11 replies
  1. Frankie says:

    Having never been in your situation, our advice does not carry the weight of experience; however, one issue that you may want to discuss is whether you guys can be good friends. A 36 year old typically doesn't enjoy the same activities as a 65 year old. In situations where couples have a large age difference, that difference pulls couples apart.

    • Sarge says:

      That has been one of my concerns. In the military I learned how to relate to my younger troops, as well as my own children, the youngest who is her age. Thank you.

  2. LovelyLonelyLady says:

    I absolutely love marriages with age differences! Many of my favorite stories (fictional and non) involve couples who have some degree of an age gap. My sister married a guy who is over 20 years older than she is, and they're super happy. Personally, I pray for an older man to marry. The Biblical story of Boaz and Ruth is one of an older man and young woman. Hollywood actors Humphrey Bogart and Lauren Bacall married when he was 45 and she was 19 or 20 and they had a great marriage. Age is not an issue if everything else lines up, like your faith, your mutual interests, dreams, and life purposes. I know that there's the concern of an older spouse passing away too early or being unable to have children, but here are my thoughts: if God brings two people together, they have the same death date they would have if they were younger; and as to the second, if a couple knows what they want as regards having kids, they will then make the choice to marry or not. I pray this helps! If the Lord is leading you and this lady together, go for it!

    • Sarge says:

      You, DefiantArtist and CrazyHappyLoved all made excellent point, thank you.
      I do believe that as long as there is love, communication, openness, and faith in a marriage age has little effect on a relationship. I’m not trying to find a younger lady because of sex per se, but for love and partnership. Sex is certainly part of the needs, but my late wife couldn’t have vaginal intercourse for years before she passed away. And I’ve been taking my sex life into my own hands for ten years. (Yes pun was intended.) Ruth and Boaz are a fine example for age differences in a healthy relationship.
      So thank you all very much.

  3. DefiantArtist says:

    I am single, so my advice may not be the most qualified, but I would say go for it. As mentioned above, Ruth and Boaz are an excellent example of an age-gap relationship; modern traditions have made so many people think such a thing would be gross or 'icky,' but I have no respect for modern traditions. If she is the right woman for you, age makes no difference. After all, our lifespans are so comparatively short anyway, and then we have eternity. Against that backdrop, what is 30 years, you know? Not even a wisp. If you are meant to be, then I, for one, wish you all the best.

  4. CrazyHappyLoved says:

    I agree with the posters who say age doesn't matter among the mature. If she were still a “child,” not only might the relationship be more likely to fail, but it might even seem predatory by modern standards. (Never mind that the young prey on each other; whole 'nother topic.) Certainly, a young mother can see the benefits of a settled, responsible, committed husband. I would caution only that you know the truth about why the first marriage/relationship failed, if it did. (Perhaps she is also widowed.) If that turns up red flags, be sure any concerns of yours are addressed. Based on what you've told us about yourself and your first marriage, I hope you will also determine to love this woman on her own merits and avoid comparing her to your lost beloved. Oh! And be sure to discuss your sexual appetite/desires somewhere along the road, if that doesn't come up in the "what happened last time?" discussions. Managing expectationsrs and hers—can be key to a happy marriage. Remember that people change and grow, and both of you will need to be flexible in different life stages. Other than those considerations, I pray God's blessing on you both/all!

  5. oldmarriedcouple says:

    Most everyone has mentioned the 'pitfalls' of the age differences, and what to be aware of before taking 'the plunge' into a marriage with a large age gap. You have the experience and intelligence to know all that. And your intentions sound forthright (a good relationship, not just sex). I would like to point out a couple reasons why I think women may be more interested in this type of relationship than the avg person thinks (ladies, feel free to correct me if I am off base).
    One is the maturity level of the man. You've already been in a long term relationship (that ended sooner than expected due to health issues), so she knows you know how to do the true relationship thing. I know some single women in mid 20's that admire my wife and I having a 42 year marriage. They can't imagine it with someone their own age, bec the women say that people of the younger generations just give up instead of trying harder. Also, I think young men of today are socially inept in many ways. In my late teens early 20s I was watching for girls (not interested in cell phones or all this other crap that distracts from finding a mate). You can't be oblivious to the opposite sex as a guy and think a girls just going to fall in your lap. And the 20's women I talk to sometimes ask how to best 'find a man'. So I give them good tips (coed golf lessons or other sports lessons-smart guys will try to better themselves and hopefully already be fit enough to play a sport. Volunteer activities where u might meet eligible young men thinking of someone besides themselves.)

    But back to the point at hand. Women want maturity (of mind) and ability (of good relationships) and you have that to offer. They don't usually want to raise another son or child. I believe intergenerational relationships (whether just friendships or romances) can be very rewarding. I would enjoy hearing about your decisions and progress in the coming months, if you don't mind sharing (doesn't have to be about sex, just how things are panning out for you and your lady friend.)

    [Not that I wouldn't also love to hear how it goes, but it would be better to connect through a forum for those updates. This site is intended to focus on the sexual side of marriage. – Missy, MH]

    • Sarge says:

      Your insight is quite similar to mine, so thank you. I don’t want to put down any of the younger men on MH, but 20 and 30 somethings nowadays don’t seen interested in long term relationships like we have, or have had. Selfishness had seeped into our young people and they seem narrow minded and set on the here and now, “YOLO” if you will.
      Thanks again, and to all others who have spoken up to give me more insight.

    • oldmarriedcouple says:

      Add to the situation is that young men I see around today (like 16 and up to mid 20s) just don't even seem interested in finding a girl to date. I've people-watched the teenagers strolling around some nice outdoor shopping areas, with beautiful young women all around, and they only have their faces in their phones for whatever reason. At that age, I was 'scoping out the scenery" and looking for an opportunity to chat up a lovely young thing with the hope/intention of a relationship. These youth I see have no chance and/or no hope of finding a girl with that behavior.

  6. SecondMarge says:

    People are living longer and healthier later in life. If you enjoy each other’s company and feel marriage will make it better, why not.

    I was married to a much older man. It was great while he was healthy.

    Now I’m dating a much younger man. Been married twice and feel no need to marry a third time. But it’s a good relationship for both of us despite the age difference.

  7. B.J.McKay says:

    I am 18 years older than my wife. Everything is very good at the present. Future will largely depend on whether I maintain my health.

    My dad died at 67, so I could leave her a relatively young widow.

    I never had any concerns about her sincerity. She's a very good and decent person- not a stripper or gold-digger type. Thus, it has been a good 7 years.

Leave a Reply

Want to join the discussion?
Feel free to contribute!

Leave a Reply