Psychic Q&A: Dating an Older Man

Psychic Q&A: Dating an Older Man

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Dear Kallista,

I’m 44 years old and dating an older man who I’m deeply in love with. His past relationships have hurt him greatly. I’ve also had my own relationship issues, but I’ve worked hard to identify them and work on them. This older man and I have been dating for about two years but have separated a few times because he won’t say, “I love you.” He claims he’s said it to too many women in his past who have hurt him. Instead, he says he will show his love. I have a hard time accepting this because I really don’t know what that means. Does he love me or not? I care for him deeply and want positive growth with him. He makes me want to be a better person and he has made a huge impression on me.

Recently, we had another disagreement. He felt like I was upset over something small, but it was important to me. Instead of talking it through, he immediately said, “I think we should take a break.” In defense, I said, “Yes, I think we should!” I regret agreeing with him and what he said totally blew me out of the water. I thought we were super happy. Since this last fight, we have not talked, yet I think about him and pray for him every day. I miss him deeply and try to send him messages of love. I know he reads them but he never responds. Is this really the end of our relationship? I feel like he could be my soulmate, but am I misguided in my wants?


Psychic Kallista ext. 9623 responds:

Dear Catherine,

There are some layers here. You are dating an older man and you ask does he love you? The answer is yes. But as you realize, he loves differently than you do. His love is conditional. He blames his past pain on prior women but ignores that he is the common denominator in all of his past relationships. He thinks if he says he loves you, he’s committing, which is something he fears—with anyone. He’s doing a lot of blaming but he’s not accepting his responsibility to behave in a mature manner in his relationship with you. Meanwhile, you’ve bravely faced yourself in doing the work you’ve done on you. Clearly, you are strong enough to ask for help. Therapy would be a great help here, for if he is to hold on to you, he has work to do—on himself.

Dating an older man who behaves in an immature way can be very frustrating. You’ve been so patient, loving, and amazing with him, but when he broke it off with you yet again, something in you snapped. Please be gentle with yourself. You agreed to the break because you needed to do so. There is something punishing and cruel in how he constantly separates from you every time you need him most. He does this because he doesn’t want to look at himself and he is trying to force you to change. He fully expects you to continue tolerating the intolerable.

Remember, we have many soulmates in one lifetime, and you have the power to choose. You’re dating an older man, and he is one of your soulmates, but you will decide how long this man gets to be with you. He has a chance to prove himself to you. In the fine print of many soulmate contracts, including yours, in particular, it says this is the most difficult relationship you’ll ever have. It can also be incredibly rewarding, and even result in marriage, but only if the work is done. Otherwise, you’ll boot this man out and open your heart to new love—which will come if you allow it.

Will he be back? Yes. You’re the best thing he’s ever had in his life. He doesn’t want to lose you. I wish I could tell you things will be a lot easier with him, but I know you want the truth. He hasn’t changed. You feel like you are at a banquet table, but he’s only giving you crumbs. You are not misguided in your wants, but you do have a rose with thorns in dating this older man.

Soon, if you are silent and do not send any further messages to him, your silence will motivate him to connect, and he will finally reach out to you. He may have done so by the time you read this. When he is again at your side, which will be by the end of this month, try giving less. Don’t say it out loud; just quietly pull back a bit. He will sense this and just naturally give you a little more. You deserve it.

Wishing you every good thing,


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2 thoughts on “Psychic Q&A: Dating an Older Man

  1. Catherine

    Kallista, I have waited several months and in February I found out he is now in a new relationship. I am unsure how to feel about this situation now. Can you please provide further guidance?

  2. Leslie Mender

    Will i be able to buy a new car? My Old car needs a new engine and i need car thats reliable. Will I find the car that catches my eye?


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