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Our May-September Relationship is Confusing

Category: Values & Beliefs

Question: Dear Luise: I’m in a very confusing relationship with a friend of mine and I keep teeter-tottering on whether to go with it because it feels right or whether to run away from it before it gets too complicated. He is someone I’ve known nearly my whole life and have always felt a closeness and trust for. We interest each other, often having deep conversations that I find people of my own age usually struggling to keep up with. We make each other laugh and are both very attracted to the other. We are a leaning-tree for each other and I feel like we really compliment each other. However, this is definitely an example of a May-September relationship to the extreme. I am in my late 20s and he is sitting at 35 years superior to me. The sexual part of it is phenomenal, though neither of us would have ever guessed it to go beyond a close friendship. However, now that we have crossed that line, we can’t get enough of each other. I care about him very much and I’m just afraid I’m going to eventually hurt him. He’s gotten very emotionally invested in this. I’m young…and not at all wanting to marry or have a family or settle down in any way, at least not at this point. I’ve been clear about that and he says he understands. Yet, I don’t think either of us comes even close to understanding what’s going on between us. I’ve contributed some really great advice on what I think would be in our best interest and what we could do to prevent added confusion for ourselves. It sounds great, but in the heat of the moment, I end up going against my own advice (leaving us even more confused as to what’s going on and “what we are”). I’ve been trying to find some information on the psychological end of May-September relationships that have such extreme generational gaps. I don’t think there’s any cookie cutter advice that would fit our situation perfectly, but I’m curious as to what others in similar situations have experienced from it. I want very much to understand the situation at hand, but can’t find anything credible pertaining to the situation. Could you help me to understand this a bit better? I’m a bit confused and want to make the right choices for the right reasons in this relationship, as we do both love each other. Having some other perspectives to consider would be very helpful! Thanks for your time! C.

Answer: Dear C. If you were going to run away from the situation before it got too complicated, wouldn’t you be long gone by now? It sounds to me like you already see it as pretty complex.

My husband is 15 1/2 years older than I am but we married late and that can change the dynamics a lot. It makes a great deal of difference how mature you are and how young at heart he is, for one thing. And for another, what your values, hopes and dreams are. Do they match?

Long-term plans are often interrupted by “life.” There are no guarantees, as you know. It sounds like your head says one thing and your heart says something else. If that’s the case, about all you can do is take it one day at a time and be grateful that love has come into your life. That doesn’t always happen, you know.

Many people never experience the kind of compatibility you describe. It’s rare. I think you might as well enjoy it for as long as it lasts, and if that happens to turn out to be a lifetime, then what the heck. I would suggest you lighten up and let go of any fear you might have about doing the wrong thing. None of us has a crystal ball and every fork in the road has its ups and its downs. Blessings, Luise

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