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I’m hoping that you can throw some light on the situation- as someone who doesn’t know me or hasn’t heard about this before. (My friends find it hard as they both know the woman involved and are probably sick of the situation too). I have found it very hard to be objective about this and have been paralyzed by indecision for over 18 months now. For everybody’s sake I need to sort this out.

I never even really considered that I might be undergoing a midlife crises until I stumbled on your site and it got me thinking!! Maybe I am? I guess generally I still feel very young at heart. I turn 40 in two weeks. I guess that is quite a milestone in one’s life.


Until now I have lived kind of a Peter Pan life in that I’ve played in a successful rock band and have always had a lot of fun. I have a lot of friends, have a great life and haven’t ever really needed to try hard with women. (Even though I’ve always been in relationships and have never cheated on the woman in my life- I guess I’ve always had a lot of fun flirting). I have a great job, investments, money, traveled – life is amazing- except for my personal life in that I can’t decide which beautiful and lovely woman to choose to be with. Both of them are wonderful and I really feel like I love both of them but in different ways as they are both quite different.

I guess turning forty is really making me think about the fact that I do want to start a family- have some kids and be a dad. I think my life would feel incomplete without having a couple of kids- and I feel like if I don’t do it soon- maybe I’ll be too old?

By the way people are often surprised when I tell them that I’m turning 40 and say I only look about 35 and I’m pretty fit and healthy too as I look after myself. I think this, along with playing in the band, has always helped me attract younger and beautiful woman. The two woman in my life are 28 and 26 respectively.

My situation … Ok first up- I have always had a problem with long term commitment. I guess I put that down to my parents divorce as a kid and in my mind I guess I’ve always felt that people come together- have their time and then, in most instances usually break up. I really don’t like the thought of marriage but I am happy to be committed to one woman. So my pattern of my last few girlfriends has been relationships for 5 years, three years, four years. I guess in the past I’ve considered myself a serial monogamist- ha ha. I’d love them, never cheat on them, but when the time seemed right it would just end. And generally I was ok with that. I also in my head knew that I’d never “settle down” (I guess that means have kids) till I guess I was around 40- but back then that seemed ages away. Like I said the big birthday is less than two weeks away.

Anyhow…. I’m in a situation that has been going on for about 18 months. My problem is absolute indecision over two young, very attractive and lovely women. One is 28, the other is 26. They are both very different but I find both of them amazing. I guess for a problem- this is a pretty good one to have- basically deciding on which one to be with. But it has been a problem for 18 months! I have caused both of them a lot of pain. (And myself for that matter). I can’t believe that I still have an option with either of them. (Though I know that time is running out with both of them). I think I thought that one of them would tell me to shove off sooner or later and I wouldn’t have to make the decision. But I still have the option of either, although I do feel like my window of opportunity could be closing with both. However I’ve felt that way for the past year and a half and the situation is still here.

For the record- up until this stage of my life I had always been very decisive and never struggled with anything like this! So this feels like the hardest thing I’ve ever had to do. Like I’m at a “T” intersection and if I turn left- my life will be radically different to if I turn right.

Anyhow lets start with Miss A.

6 years ago I fell madly in love with her- I still feel like she has been the woman whom I have loved like no other in my life and I guess for the first time in my life I thought she might be my life partner- mother of my children etc. I even moved 1500 kilometers to be with her. Quit my amazing job, left all my friends, potentially sacrificed my position in the successful band (although the band still worked out) and moved to be with her. Truth be told- I wanted to move where she lived but she was the catalyst to move so to speak.

We generally had a fantastic relationship for four years. A few ups and downs but generally fantastic- good friends, sex, fun, adventure etc.

However she wanted to get married- I didn’t and this caused her some pain and our relationship some grief. She couldn’t understand why if everything was so great and that I really loved her- why wouldn’t I marry her. I explained that in my mind she was already my life partner, what was mine was hers and we didn’t need to get married. I was honest and said I didn’t believe in marriage and that I thought it was an outdated institution that revolved around a expensive ceremony and a piece of paper. True commitment was staying together in a loving relationship. But this hurt her. I one day made the mistake of telling her- sorry but I’ll never marry you. (Dumb I know).

Anyhow after about four years we grew apart (whilst still living together), I was so confident about her love for me I became almost arrogant- e.g. her saying we really need to talk and me saying- go to sleep, I’m tired, everything’s fine. (Dumb I know) We were both very busy and focused on our careers. Next thing I know I find a sexually suggestive text message on her phone one day from another dude. (I didn’t normally check her phone or anything, but on this day she’d left it home and I guess I had started to suspect something by her new growing distance). She swears to this day that up until then nothing had happened. But when she told me she was confused about her feelings towards me and this new guy-and told me she needed some time to assess her situation- I told her she’d should move out. (It was my house we were living in). It was very very, very painful. I was devistated- in shock. After a short time I tried in vain to talk with her- pleaded for her to come back and be with me but I think the other dude was very convincing and moved in on her. My guess is that they were together on and off for maybe around 1 year. (Maybe less) Although I can’t be sure of this. I know they were together though for a considerable period.

Basically I was an emotional wreck for about a year. We kept in touch, I had a brief rebound sexual fling with another woman. It meant nothing. And then Ms A and I decided to become friends again. (Going to movies, dinner, etc. but initially no romance. I think we were both too cautious and hurt). Although by now I just didn’t trust her and it just didn’t feel the same anymore. I felt like I still loved her very much, but I couldn’t give myself to her again. When we had sex it was like- I was saying in my head- “This just doesn’t feel right”. (We had a couple of sexual encounters together. It was very hard for me to reconnect with her physically, although emotionally I still cared deeply for her. In her mind she thought we were reconnecting through sex- I guess I was just engaging in it to see how it felt. After a couple of failed attempts for us to get us back together- both of us feeling damaged I guess I made a conscious decision to try move past it. I still loved her very much (I still do) but I was sick of the situation. She had been my greatest love, my best friend, but I felt trapped. Unable to find what we had on that level. She wanted me back- I still loved her but couldn’t reconnect physically (which was weird cause our sex was once smoking hot). I could feel she was trying to win me back but I thought I just wanted to be friends. After initially ditching me and not wanting me back she has chased me very hard for nearly two years. But like I said- two years ago, although I loved her and still had visions of a future with her (kids etc), the sex felt- well basically wrong. But it’s been a weird ride because I just couldn’t let her go and be free? How messed up is that?

And because of this I allowed Ms B to come into my life. After a few months of getting to know each other Ms B made it very clear that she was very very interested in me. As Ms A went away for work for a few months and basically Ms B and I began a relationship. Ms B is very different to Ms A but the excitement of a new relationship and the feeling of finally moving on was great. Amazing sex and even with the amazing sex removed from the equation- Ms B is still a very beautiful (inside and out), genuine and wonderful person whom over the previous year and a half- her and I have become very very good friends.

She at the time of us hooking up had no idea of the emotional baggage I carried over Ms A. And to be honest neither did I. At the time I can remember thinking that It wasn’t the same with Ms A and I felt like I was in relationship limbo and I needed to move on. I thought at the time that if I moved on with Ms B then Ms A would just sort of say- “ok I understand- lets still be friends”. I was very wrong. And even though it had been a long time since I had been “together” with Ms A- I underestimated the emotional response I would have when Ms A actually told me (rather than just hinting) how much she still loved me and wanted me back. But by this stage I had become involved with, and very fond of Ms B- Not to mention that the sex was exceptional and often!

When Miss A came back from working (whilst I had started the relationship with Ms B) she sent me a heart-felt written letter stating how much she loved me, how she believed we were meant to be together, how our relationship could be even better than it was, and how all our dreams from the past could still come true- house, kids, dog, etc., etc. That letter really rocked me! I felt very sad about this and guilty. I told Ms B that I needed space and I told her all about Ms A. She was shocked, upset, but inevitably undeterred. She continued to chase me as well. (As did I chase her when she broke it off with me). I felt that although I had this long history with Ms A and still loved her- all the failed attempts to get together in the past had been so frustrating. Not to mention Ms B was such an amazing person and we got on so well and had so much fun and connected deeply physically which I must admit- we still do.

I told Ms A that there was someone else that I had met who I now cared for deeply too. She was upset and I was confused- I called it off with both of them but then Ms A went away again for another four or five weeks and in that time i hooked up again with Ms B.

Anyhow I could go on and on about my adventures with Ms A and Ms B- but ultimately what has happened is I did the wrong thing. I went from being with Ms B- telling her I needed a break, having a break, trying again with Ms A, telling her I needed a break, having a break, going back to Ms B and repeating the same scenario many times over the previous year and a half. In the process I have caused a lot of hurt and confusion for everyone involved. I know that both of these woman still love me, but I also know I’ve caused a lot of pain and scars.

I am not a bad man and I never intentionally set out to hurt either of these woman but in hindsight I can see that my indecision and weak choices have caused a big mess. I ended up getting into a situation where I told both of them lies because at times I was living a double life- even though I was telling lies to try not hurt either of them whist I tried to work out which one I was meant to be with. I guess I kind of feel like its Ms A whom I’m meant to be with- Perhaps due to our history and past visions of our future, but when I’m with her- the love we once shared is not the same and I can’t even be intimate with her. I don’t know if that is due to guilt, or the fact that I have such amazing sex with Ms B. (Which is weird because Ms A is a very attractive woman- most guys would kill to be with her).

And with Ms B- our friendship is great, she is so wonderful and funny, friendly, beautiful, would be a great mum etc- but I can’t completely give myself to her because of my love for Ms A. It’s a really messed up situation.

Ms B generally new just about everything about Ms A, but Ms A really had no idea about Ms B. At the start she new of her existence but I told her it was nothing and that she had now disappeared. ( A complete lie- something I feel very very guilty about and wish I hadn’t done).

Finally and recently Ms B contacted Ms A and told her what had been going on- at least her version of events. Ms A was shattered and now, although I know she loves me, will find it very hard to trust me. She is very hurt and saying to me that she doesn’t know if she can ever forgive me for the deceit. And I’m sure she is still torn between writing me off completely- or waiting for me to come and beg forgivness and see if we can try be together again.

Ms B said she can forgive me and move forward. We have been intimate since this happened. And although sex has been a big part of my relationship with Ms B- I am well aware that eventually it will die down too and I still can see what a great woman she is and can see a future with her too.

I probably sound like a real screw up to you and I guess I am. Like I mentioned earlier- up until now I have always been honorable and decisive with things like this. I don’t want to be a bad guy that jacks people over.

I tried to get back with Ms A because she has been the woman whom I have loved the most in my life. She was the one I sacrificed everything for and who I though would be my woman and mother of my children. I love her dearly but the last time we tried to sleep together I couldn’t even get hard- even with her giving me oral. I saw a psych and he told me my lust would return for Ms A if I stopped seeing Ms B.

I guess I’m so worried about making a fatally wrong decision.

What are your thoughts on my situation?


Thanks for writing in.  Let me start with a couple of things.  First of all, on behalf of all midlife bachelors – I want to congratulate you for having relationships with two different early- to mid-twenties hot women.   You are our collective hero, Sir!  At age 40, you have experienced things that the rest of us pretty much dream about.   Well done!!!  Secondly, the next time you are in the Los Angeles/Orange County area – let’s have lunch.  I would have suggested that you let me party with the band, but my current girlfriend would kick my ass for that … ha ha ha.

Okay – your email was the longest I’ve ever received at ASK MIDLIFE BACHELOR.  Let me distill the situation down to the core issues, as I think I understand them:

  1. You believe you need to choose one of these two women, and possibly get married.  The reason driving this is – you feel like it might be time to have children.   Your biological clock sounds like it is ticking … you are having a midlife crisis of sorts.
  2. You love Ms. A, but because of your history together – you have difficulty having sex with her.  You feel like she is “the one”, but there are trust issues on both sides.
  3. You have awesome sex with Ms. B, but because your head is caught up with Ms. A – you don’t feel it is right to commit to Ms. B.
  4. Ms. A and Ms. B have talked, and can contact one another at will.   This is a tremendously important parameter to your situation.

First of all, in my mind – the ONLY reason to get married is if you want to have children.  Otherwise in this day and age, getting married can easily wind up being a losing proposition for the larger income earner involved – which is obviously you.  Remember – marriage is the number one cause of divorce.   Sounds ridiculously simple, right?  Many people forget that – so I state the obvious, and I’m not joking!  My point – don’t get married unless you want children.  Otherwise, there is nothing wrong with “serial monogamy” – which is exactly what I, myself, practice (although I am divorced).

Now regarding Ms. A – I know exactly how you feel about her.  I, myself, have a certain woman in my past who I can never seem to get out of my head.  In her case, she cheated on me – and when we were together, she made my life hell at times … but we had the most awesome sex (BEFORE she cheated on me).  But after we got back together (after she cheated on me), I had a lot of difficulty having sex with her – just as you describe is the case with you and Ms. A.  Our situations are different, of course, but there are similarities.   The best advice I can offer you is – you need to properly resolve your relationship with Ms. A before you consider committing to Ms. B or anyone else … otherwise Ms. A will always be in your head, and you’ll perpetually be in the same situation you are in right now.

The sexual issue that you mention with Ms. A is a big one.  Have you tried Viagra or anything similar?  If you have, and you still don’t feel able or right about having sex with her – then that is a huge input for your long-term decision.   Can you commit to someone who doesn’t arouse you (for whatever reason)?   And (just to point out the obvious) – you are a rock star, and will have plenty of opportunities to cheat, if you are not happy at home … do you want to put yourself in that position?

I believe what I would do if I were in your shoes is call it off with Ms. B, and fully commit yourself to Ms. A.   Give your relationship with Ms. A time – and see if the sexual issue goes away.   How much time should you give it?  I don’t know – I think you’ll know for sure when it is judgment day.  But I wouldn’t marry Ms. A until you’re certain about her, and the relationship.   Again – if you don’t fully resolve your relationship with Ms. A, then it sounds to me like she will always be in your head … so give it one last chance, give it your all, and see how it goes with her.   After some time goes by, you will then have a true “moment of clarity” where you will know with certainty if she was the right choice for you.

With respect to Ms. B, tell her the truth – tell her that you need to fully resolve this other relationship before you do anything further.   Now normally I’d suggest that you ride Ms. B one last time, but since Ms. B and Ms. A can contact one another at will, you have assume that whatever you say or do with one will become known to the other.  I’d tell Ms. B that you can make no promises about the future – that you need to cut off contact with her until further notice (and that could be forever).  [If you don’t cut off all contact with Ms. B, then you will not be able to fully give Ms. A the chance your relationship with her needs.]

Now recognize that a likely/possible outcome is that you wind up with NEITHER of these two great women.  If that is the case, then I believe it is FATE.  Everything happens to us for a reason – and that reason could be that you are meant to be with someone else … someone you may not even have met yet.  With all of this kind of stuff discussed here, it is all one big learning experience – and it is a great thing to share it with others … so that they can learn without necessarily having to go through some of these trials/tribulations themselves.  This sharing/learning is the mission of … that’s what our motto on the graphic at the top-right of the each web page means, “Leverage the midlife knowledge”.

Worst-case, you are a rock star – and you can certainly feed your appetite from the women who follow your band … but it sounds like you want to be done with that phase of your life.  If you want to live like the rest of us, you might look over the Midlife Dating Advice section here on   There are useful sections there, such as:

Fundamental Truths about Women and Midlife Dating Today

Midlife Bachelor Personal Makeover

Develop a Strategy for Midlife Bachelor Success

Reaching Midlife Bachelor Equilibrium

Not all of the above links apply to you necessarily, just consider it good food for thought.  We also have a very good Midlife Forum here where both men and women post about midlife dating and relationship issues (along with other things, too).  I encourage you to become a regular member of our community.

Good luck – I hope my input was helpful.   Please let me know how you proceed, and how things turn out, okay?

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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.