Stop Fearing You’ll End Up Alone

Name: Cara
Age: 50
State: New York
Question: Moxie, I wrote in before with a question regarding my older (8yrs) white boyfriend who was not introducing me to his family/friends.   You and your readers suggested that I leave him because this relationship wasn’t going anywhere.

I hung in for another 6 months because I wanted to believe that he would finally do it.  In that 6 months time, he did not but on top of that I caught him cheating.  I broke up with him and haven’t spoke with him since.

Since Hurricane Sandy he reached out to me and we have been cordial…now he says he is ready to truly committ to me, wants me to meet his family next week (they will be in town for the holidays) and wants to go ring shopping now.  He says he has realized how empty his life has been without me and wants me in his life.  He wants us to be married within the year (sooner if I agree to move in with him).

I am 50 years old and to be honest the prospects out there of men in who want to settle down are almost nil.  It’s been almost 2 years and although I’ve been dating in that time, most men I’ve met just want something casual where I want to settle down.

Am I in love with him….NO, and I’ve told him so.  But I do care about him still.  He says he will do ANYTHING/EVERYTHING to get me back and show me he is the man I fell in love with 4 years ago (that’s how long we dated).  But at this time, I don’t trust him and I don’t know if the love and trust I felt can come back.

Marrying him will afford me a nice lifestyle (big house, fancy cars, vacations, etc), but I want to marry for love and companionship not just financial security.  I’m just confused about my feelings, my life, my choices, etc.  I don’t want to be writing to you in 5 years regretting not giving him a chance.

Is it really once a cheater always a cheater?  Can people really change?  Please help!



So, it took him to almost 60 to realize how empty his life was without a partner? Meh. Not buying it. This feels like a case of The Holiday Blues combined with him coming face to face with the reality that he ain’t getting any younger. For me, that’s not a good enough reason to strap yourself in for the rest of your life.

Take a look around. You have settled down. You’re in your fifties, you’ve obviously got a life and a job and a sense of stability. You don’t need a man to settle down. You can take a partner so that you have someone with you on the journey, but the settling down part is on you. And you’ve done it. You’ve gotten this far without a manz.

Date this guy. Enjoy his company. But don’t commit to him because you fear you have no other options left. Even if that’s true, that’s still never a reason to make a life-long commitment to someone.

Will he cheat again? I don’t know. I’ve said before that I don’t feel that the cheating is the real issue and that it’s just an outlier. The real issue is that, by stepping out with someone else, he clearly doesn’t value the commitment he made to you. That’s just another sign of someone’s poor judgment and willingness to make an empty promise. People with these characteristics don’t tend to make the greatest of partners. I don’t believe those people will change at their core. They might not cheat but they’re still the same people. Especially this guy who is knocking on 60 years old. The thinking that drove him to cheat likely won’t change.

Choosing whether or not to be with someone shouldn’t involve this much internal conflict.


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12 Responses to “Stop Fearing You’ll End Up Alone”

  1. ISOf16 Says:

    He has a “nice lifestyle (big house, fancy cars, vacations, etc)” What is his phone number… I will marry him :-) HA Ha……

  2. fuzzilla Says:

    Agreed, but I don’t think she should date him; she’d be in danger of getting sucked into his “no, it’s different this time” bullshit. Although if she doesn’t love him maybe she could salvage an FWB thing out of it.

  3. wishing u well Says:

    Hurricane Sandy sparked a LOT of attempted dating reconnections. Combine that with the holiday season, and Moxie has a valid point. I’m not a fan of his attempt to reappear and go from 0 to 100mph quickly. As romantic as it can “seem,” this isn’t a movie. It’s just too easy to kick the real, unresolved issues of the relationship under the carpet while getting swept up in the glitter of planned upcoming nuptials. What of his character? Integrity? Take the time to slow things back down with him and see if he’s really serious about what he’s saying. Actions speak louder than words. I wish you well.

  4. VJ Says:

    Good advice from Moxie: “Date this guy. Enjoy his company. But don’t commit to him because you fear you have no other options left. Even if that’s true, that’s still never a reason to make a life-long commitment to someone.” they’re not the po

    If everything you say is true and you still feel like you love him? You might try again. This is not a license for the usual ‘holiday Great Expectations’ game or whatever sort of wish fulfillment fantasy he may be working here. On himself and/or you with the usual ‘Lifestyles of the rich and/or comfortable’ edition.

    So there are some rational expectations here that might be met step by step. Meet the parents, perhaps they’re not the clueless ogres he or anyone else might imagine. If that goes well, see if you might rebuild trust once again. Clearly the cheating hurt, but it’s not all that uncommon either. If you can better understand what motivates him and causes these ‘incongruities’ in his behavior or his rash/bad actions or inactions, maybe things will seem a bit brighter. But there’s no harm in just ‘waiting & seeing’ what plays out. If he’s indeed ‘smitten with you’, perhaps it’s time to test what that means this time. This may be the last chance throes of an older player, who knows? But it’s still true that neither of you is getting any younger, so why not see if he’s learned from his past mistakes? It can happen, even at advanced ages!

    But every adult over a certain age should be comfortable with their own company & know how to be ‘successfully’ alone and to be ‘their own best company’. Sadly, that seems to get rarer by the decade. Yes, and this is what they made pets for too, BTW. Cheers & Good Luck, ‘VJ’

  5. Matt Says:

    If this were a Lifestyle Original Movie, I’d say yes, take him and never let him go. However, in the real world, this guy has problems. It didn’t work before, I don’t see it working again.

  6. Howard Says:

    Tell him the truth, that you don’t love him, but you are willing to give him the chance to woo you again. Tell him that you have no intention of doing commitment with him unless he wins your love again. Meet his family as being just a friend, not any of this getting married next week stuff.

    All men are cheaters at some point in time. Don’t listen to any female balooney perspective on that. Men are indeed strange creatures. When a man decides he has had enough of the fooling around, he literally goes out and marries the fist available woman. Women just never ever get that. I don’t care how much undying love a man is professing or how well he treats you or how he only has eyes for you, if he is not ready for settling down, you are not getting commitment.

    The unfortunate reality is that a lot of men are not looking for settling down. It is not a permanent state. Really young men are like that because they feel they would be missing the world if they settled too early. The older “been burnt” guy or “having the ball too much in his court” or “experiencing sweet freedom after a divorce” can be like that too. Even the guys in the middle may be having so much fun for settling down.

    I have no idea what the percentages are, but I would say less than half the guys out there are looking for a situation where they settle down. In some circles less than 10% of guys are looking to settle down. What you have here is one of the unicorns who is actually willing to settle down. What happens with these guys at that age group with money, are too many options. The game is definitely in their favor so they imagine they have to enjoy that benefit. Of course at some point, the player recognizes it’s just a game where players really have nothing and conquests are really meaningless.

    Don’t listen to these women on this site.There are not too many of these guys out there. Give this guy a shot. Not marriage right now but the chance. Don’t keep him on ice with foolish testing and suspicious behavior. In fact lull him and give him the chance to screw things up himself. Even tell him he has competition too. That will light a fire under his butt.

  7. Nikki Says:

    OP –

    STAY AWAY!!!! Let me tell you a story about a friend of mine in Cali:

    Sherry dated Miles for more than 25 years. He was (and still is) beyond handsome. His family was her family. It was bigger than just about the two of them. She loved him beyond words. And he always said he didn’t want to get married. However he was quite the Casanova…dating around, cheating around, the works. For a long time, Sherry just ignored it. Then one day about 10 years ago, she got sick of it (and him) and dropped him like a bad habit.

    She was 50, still single, and on her own. Rocking and rolling. She would have done great, but then Miles called her up one day; he had cancer and all he could think about was being with her. Married and fulfilled. Well, Sherry took him back (who wouldn’t really). She supported him, and nurtured him. And he wasn’t alone during the process. They were a couple and he finally proposed. No ring, but he did ask, and she said yes.

    Well, wouldn’t you know it? The year after he went into remission, he “forgot” all about the fact that they were engaged. Came back with the same old line that he just “couldn’t be tied down.” And he left her before the end of that year. Our friend lost 35+ years with this lowlife. And all she had to do was let him go.

    Don’t kid yourself. People NEVER change.

    “When people reveal themselves the first time, believe them.” -Maya Angelou

  8. mari Says:

    I would date him, meet his family, but NOT go ring shopping, move in etc…find that 100 MPH behavior bizarre. This time around, watch the signs, see if he is committed, figure out what has changed (hurricane sandy?), and then go with your heart. I would not get married, move in, or anything else for a little while. You still have family and friends to meet, dates to go on..and then judge from there.

  9. LostSailor Says:

    Cara: Moxie is right, you already are settled down. Either you don’t appreciate what you have or you think you need a man to complete your settled life. I can understand both, but if you haven’t found that man to settle down with at 50, you’re going to have to squarely face the fact that you’re probably not going to. Be happy with yourself instead.

    Actually, if you can do that, it’s quite liberating, since you can enjoy the time with the men you’re dating without worrying about wasting time not finding the guy to settle down with. If he’s out there, and you’re meant to find him, it’ll happen. It’s probably more likely if you don’t have the expectation anymore.

    Now, on to your guy friend. First, any man that suddenly reappears after two years, professing undying love, and pushing hard for marriage as soon as possible, well, he has an agenda, and it’s probably not for your benefit.

    You’ve said you don’t love him and you don’t trust him, yet you’re still considering it. Whether it’s for the fancy lifestyle, I don’t know. I really have no idea why you would even consider marriage to a man you neither love nor trust, since they are both the foundations of a good marriage.

    I’m near your age and divorced. My ex and I are still friends, thankfully, but take it from me, just “caring” about him will make for a miserable marriage.

    Contrary to Howard’s comment above, not nearly all men cheat. But those who have a history of it will likely do it again. At near 60 he’s not going to change…unless something has scared him shitless, like illness.

    You say you don’t want to write Moxie in 5 year regretting not giving him a chance. Would you rather write in 5 years after a miserable marriage, heartbroken and used?

    Your call…

    • Howard Says:

      It all depends how you define cheating. if you define it within the confines of extremely committed relationships like marriage or engagement, you are absolutely correct, all men are not cheats. I did 20 years of marriage without ever straying, so I know. If you are talking about the early stages meeting someone and straying or kissing more than one woman because you are dating more than one, then all men probably cheated at some time, even if it was only in their mind or early overtures to other women.

      What I typically find is that women like to hold men to the latter standard, so given that reality, all men have cheated at some time by this harder standard so hence my comments about all men having cheated at some time. I no doubt guess, most women too have cheated if we apply the harsher standard. I do realize that when woman date more than one, they like to hypocritically insist, it is not cheating, she is just exploring her options. Interesting how women get they way it should be when its judgement time for them.

      Human beings, men and women are capable of commitment. It is however ludicrous to call someone a cheat when serious commitment has not been given. They are just exploring their options.

      • LostSailor Says:

        Howard, you seem to at least approach the truth, if from a round-about way on the left flank.

        You can’t be cheating until you have made a commitment. Dating several women at the same time isn’t cheating. Cheating necessarily involves the breaking of a promise, and if you haven’t promised to be exclusive, then there is no cheating.

        So your statement “All men are cheaters at some point in time” is bunk.

        But the man in the OPs letter is clearly no good for her. Better for her to live her life for herself instead of accepting someone who is more likely to leave her heartbroken and soul-crushed 5 years down the line…

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