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The Perils of Falling In Love With A Woman Going Through Divorce And End of Affair


The Perils of Falling In Love With A Woman Going Through Divorce And End of Affair


Miss A,

I am writing to you so that I can get some advice.  I thought maybe if I got a savvy woman’s perspective, it would be beneficial.  I developed a very close and strictly platonic relationship with a Mom from one of my children’s athletic teams.  We had lunches, coffee, and even hung out with her husband.  He traveled a good deal, so we had dinners, our children, her, and I.  She helped me with decorating, picking out clothes, and cooking…. all areas that as a single father, I was completely lost.  It was truly a multi-dimensional and completely above board relationship.  I never saw her as a potential partner.  However, one day she told me she was having an affair and that she was splitting from her husband.  It was shortly after that bomb, that it dawned on me that Mrs. X could be a potential partner.  The guy she was having an affair with, dumped her, and went back to his wife.  I helped her through the “breakup,” her separation, helping her negotiate a property settlement, and even paying for her attorney.  We had some talks about what US would look like.  I always said I did not want to have a fling with her and ruin our incredible friendship, and that if we dated, I did not want to be her first, but rather her last first date.  I told her that I truly desired a relationship whereby we actively supported, encouraged, and motivated to bring out the best in each other.  However, I knew that, if I saw her dating other guys, it would be really kind of weird and difficult for me.  She knew we were close, and had unmistakable chemistry, but she did not know if there was going to be “incredible physical chemistry” between us.  One night we talked on the phone until 3 in the morning about seemingly everything about our lives.  I went through two cordless phone batteries!


One night shortly after she separated, she was overwhelmed with single motherhood, and I came over with a bottle of wine and some small fun gifts to cheer her up, and she made her move on me.  Her fears of no physical chemistry were quickly put at ease.  What followed was 8 months of fun, closeness, and me, after 5 years of healing from a bitter divorce of a 12 year marriage, feeling loved like I had never been previously loved.  She began wedding plans…. who to officiate, who would be invited, where, when, how, etc.  My parents met her and thought we were great.  I met her parents, and they agreed.  On her own she professed her love for me to my parents, as I took her children for ice cream.  Multiple mutual friends cornered her and told her she should date me.  One friend told me she had never seen Miss X so happy, and thanked me for bringing such joy to Miss X’s life.  A number of people commented that we were meant to be together.  We tried to be very discreet as she was newly separated and her children were adjusting and she did not know just how appropriate it would seem to others to have such a serious relationship so soon after separating.  We designed a home together to accommodate all of our children and potential grandchildren down the line and I set about beginning to build the home.  We went to the beach one weekend, and had an absolute blast.  Two weeks later, she became very distant, not returning calls, delayed returns of texts.  She was not herself.  I asked her what was up.  She asked to meet me at Starbucks the next morning 45 minutes before her work.  I then realized what was up.  A defined time at a public location after very little interaction for two days, the break-up talk.  She said that she could not be in a relationship with me or anyone else.  She needed to be on her own in fairness to her children, and that being in a relationship so soon after separating was wrong.  I was crushed and had a difficult time separating from the relationship, as I thought I had truly found love, and she had loved me like no other.  She thought the best thing for both of us was to have “space,” which I have respected.  It has been almost a year.  We have had limited direct interaction.  A month after “the breakup” we both attended a mutual friend’s wedding in which she attended with the , guy she had the affair with (weird).  A couple times saying hi as we passed at the gym.  Mutual friends have told me she has been dating including a guy 10 years younger, and another guy with 4 children very young children.  She has moved on, no doubt. 


I am having trouble moving on.  I have tried dating with no real success…. One girl I met was ten years younger, great body, very smart, and was totally into me.  However, I realized I was still pining over X, and it was not fair to my new girlfriend.   I live a mile from X.  We have a number of mutual friends, go to the same gym, and our children are in the same schools.  It is hard to pretend that we do not know each other and also when I see her not to reflect back on what could have been.  At the core of me, I just miss my best friend, but even deeper I really wonder if I will ever have the same feelings for someone that I had for her.  Bottom line, what should I do?  My heart says to hold out hope that she will date others, but never find a truly deep connection like she found with me, finally realize that, and eventually come back to me.  My head tells me that I deserve someone even better than her, but where, and when, and how?  Should I hold out hope that maybe we will come back together sometime?  I know I have to move on, but how?  Please help! Thanks Miss A!! 


-Devastated Dad in DC


PS If you know of any supermodels, I run marathons, am 6’4, and have been told I am handsome!  Do not want to sound cocky, but I am a CATCH!


Dear Devastated Dad in DC,

Thank you for trusting me enough to share what you are going through. Though I don’t really consider myself a relationship expert, I will share my take on your situation. It sounds like you played the rescuer to a woman who already had two men in her life. I’m not sure how you didn’t pick up on all the “red flags”. I feel badly for you, but she wasn’t truly emotionally available when you met her. I’m also not sure that this woman is emotionally stable and prepared to have a relationship with anyone. I would advise her to take some time away from men and dating and to find out who she is now that she is divorced, and to figure out what she wants for herself and her children, and to set out to accomplish some of her own goals.

You mention that she was worried there wouldn’t be physical chemistry with you. My suspicion is that she was never really attracted to you and didn’t see you as potential boyfriend/husband material. This is why she was able to open up to you about her problems with other men currently in her life. Women who are attracted to a guy aren’t going to treat them like a girlfriend and chat about the other men in their life. I’m not sure if you are familiar with Ladder Theory, but it sounds to me like this woman had you on her “Friend Ladder” and tried moving you over to the “Real Ladder”. I feel badly for you. I think you gave too much to her. I am shocked that you paid for her divorce attorney, and that she accepted that. It’s bad, but there are women out there who are able to stomach forcing themselves to have a physical relationship with men they aren’t attracted to in order to gain money, power and fame. It seems like she definitely took advantage of your feelings and generosity. In the end, she wasn’t really attracted and couldn’t keep up the charade.

You should see this opportunistic and unstable woman for who she really is and idealizing your “friend”. I don’t think that she treated you fairly. For all we know she was seeing the guy she was having an affair with the entire time she was with you. I don’t know how you were ever able to trust this woman to begin with. I would suggest that you take a break from dating and try to get yourself straight. Beware of women who are looking for a Knight in Shinning Armour to rescue them. Typically, once they have been saved and are no longer a “little broken bird” they take their strength and fly away. Look for a woman who has her life in order and isn’t involved with multiple men. I feel like you need to work on you and how you feel about yourself. I feel like if you had more self-respect and self-esteem you would have run when you saw the warning signs.

I’m sorry if this was harsh. I hope it was helpful and that you will learn from this so you don’t go through this pain again. Please don’t idealize this relationship. It was very unhealthy. It’s women like Miss X that lead men to believe that women don’t like nice guys. Please don’t become jaded thinking that is true. I hope that in the future you will learn to protect yourself by being a better judge of women. Unfortunately, you gave more than you should have to a woman who wasn’t available or attracted to you, and who wasn’t in a healthy and stable place in her life. You ignored many “red flags” and gave your love and kindness to the wrong girl.

– Miss A



In 2008, I launched AskMissA.com which grew from my personal blog into a site with 700 writers, covering the intersection of charity & lifestyle in 20 U.S. cities. With Charity + Life, I am going back to a personal blog where I can share my favorite things, and continue to shine a light on nonprofits, and cause marketing campaigns to inspire others to give as they live.

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