Ask Ava: Dating Multiple Women

Q: Dear Ava. I am a divorced male. I met a married woman on a news blog. We decided to meet and spend some time at a motel. She is my age and loves her husband who is much older and impotent. We live 1000 miles apart and hook up twice a year.We are in computer contact all year. This has gone on for 4 years.

Two years ago I accidentally ran into a childhood flame… who is now divorced. She also lives a thousand miles away but has family near me. We started to date on her visits; and after a few times, we ended up in bed. She also IMs me and emails me.

Both say they love me… and I love them both. The married one is far ahead in bed. She is in the “advanced sex class” so to speak. The divorced one was very shy and needed coaxing to finally get her to “talk dirty”.  Now she loves to do it when we chat. She even expresses an interest in lite bondage.

Let me cut to the chase, Ava. I bought a house near the married one… and intend to move there in a year or so. I feel a little guilty with this. But I can’t say it’s not a pleasure having them both. But it has to end… Or does it? I hate to hurt either of them… Btw I’m not a player… by nature. I was faithfully married for 22 years.

This a totally “computer generated” drama (laughing). Do you have any advice on how to handle this?

A: Dear Jerard, Thank you for your well-written, detailed letter. All too often, readers send questions without enough information for me to respond to. Your question gave me much to think about.

Saying your situation is complicated is an understatement, so I can see why you wonder if things have to end. I don’t judge affairs because I think they start when there’s a problem in the primary relationship; and when an affair continues for an extended period of time (as with yours), there must be a deep, meaningful connection (more than sex). Your first relationship feels solid, but…

I think, although by accident, you entered into a second relationship because there may not have been enough “in person” contact with Lady 1. Perhaps it requires two women to fulfill all your needs. And maybe this “part-time” commitment to both women is an unconscious way to avoid another long-term monogamous union (you didn’t give details about the end of your marriage.)

I believe that your feelings of guilt and worry come mostly from adding Lady 2 into the mix. I’m assuming neither women knows about one another (a complication that would make any man uncomfortable, sooner or later). I feel your loyalty lies with Lady 1; you have a longer history, you are planning to move closer, and she seems to be a more suitable lover.

You could cut off your relationship with Lady 2. This would allow you to focus on Lady 1 and give Lady 2 a chance to move on from her divorce without more heartbreak. Plus, I guarantee, you will feel less stressed. If “the husband” doesn’t know about you, is there any way of Lady 1 revealing your relationship that he would accept? Most people aren’t progressive enough to see this kind of “open marriage” as a way of keeping spouses together and happy, but I do see it happen, and with fantastic results.

If being “the other man” is not enough, perhaps you’d like to take a chance with Lady 2 by breaking it off with Lady 1. What do you desire long-term? Do you see yourself with one of these women down the road? Do you want a serious relationship again?

Jerard, I’m sorry I can’t give more concrete advice, but I hope some of my impressions and thoughts about your situation will help you to make a decision that brings you peace and harmony.

From my own experience, dating multiple people was fun and exciting, but only when things remained light and/or when there was honesty about the situation between partners.

Need advice on dating, relationships, or sex? SUBMIT YOUR QUESTION HERE, and who knows, you may appear in the next Cougar World newsletter. -xo Ava

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