Dear Jennifer,

I am an intelligent, attractive woman in my early thirties. I have been dating for over a decade and I am emotionally exhausted. After so many disappointments, I basically threw in the towel and said, “Hashem, I surrender to You. If You want this to happen, it will happen, and if it’s not in Your plan, then it won’t happen.” A few months later, a wonderful man came into my life. We have been dating for a couple of months and are going to be engaged soon.

I couldn’t be happier. But my best friend does not like my boyfriend and fills my mind with doubt. She and I have been single together all this time and have been through it all together. She is my closest friend and a wonderful person who devotes her life to work and chesed. Because of her character, I know that she is not out to sabotage me.

When I am with my boyfriend, I am on a cloud, but when I am with her, I am worried. Her main concern is that he was married before and has a child. She has heard rumors from his ex’s family and friends that he was not a good guy. When I press for details, she has nothing specific to share. She worries that being a stepmother is not the ideal situation for a woman who doesn’t have her own children; she says it’s not fair and that I should break up with him and hold out for a guy who doesn’t have an ex-wife and kids.

I have shared my concerns with him and have done a normal amount of research on his family and background. Some people go into detective mode, but that is not my style. He has told me his side of what went wrong in the marriage, and he seems to own his part in things and even talks about lessons he has learned and what he would do differently. To me he seems enlightened. He is a wonderful co-parent, and when I am around and he is talking to his ex, they are friendly. I met his ex-wife twice and she was friendly to me as well. She speaks highly of him, as he does of her. They just weren’t a good match. I really don’t think there is some mysterious awful thing that happened when they were married.

I went so far as to invite my best friend and boyfriend to dinner so we could all sit down and talk. My boyfriend liked the idea of clearing his name with her, but she refused even to sit down with us. It is important to me that my best friend like my future husband. I hate all of this division. I feel as though I have two separate lives, and I want them to fuse and for things to feel normal.

I told my friend we are about to get engaged because I wanted to prepare her so she can be there for me emotionally. She told me she does not support this marriage; she thinks I am making a grave mistake and can’t celebrate fully, but because she loves me she will attend everything.

Am I missing something? Is she seeing something I am not seeing? My parents aren’t frum; they don’t get any of this, so I really don’t have anyone to turn to other than my friend. Can I get married without the support and berachah of the person closest to me? I hate this situation I am in. I want go through this wonderful time of life with her and for her to share in my joy. Is there anything I can do to get her on board?


Torn in Half


Dear Torn in Half,

First, I want to acknowledge your upcoming engagement. Without wishing you a mazel tov, I will say b’sha’ah tovah. You have paid your dating dues and you have met Mr. Right. Except that your best friend is convinced he is Mr. Wrong because he is divorced with a child and because there are rumors that he has behaved improperly, though she has nothing of substance to report. I feel your pain and I am so sorry you are in this position.

You asked, “Is there anything I can do to get her on board?” You shouldn’t have to do anything to get her on board. Unless she has something specific and accurate to report to you, she should be your biggest cheerleader. It is not your job to convince her that your guy is the right guy for you. It’s your job to enjoy your guy and your life! Your openness to your friend’s apprehensions impresses me. Many people would be quick to dismiss a negative opinion. It seems you have listened, observed, and watched out for her concerns but you came up empty.

Some of your friend’s behaviors concern me, and I wonder if you share my sentiment. The first is her personal feeling that divorced men with children are not suitable for a single, never-married woman in her thirties. She is projecting her own thoughts and feelings onto you. Perhaps she would not consider entering a relationship with a divorced man. That is her prerogative. Perhaps she is not up to the job of being a stepmother and having a relationship with someone’s child and ex-wife. That, too, is fine for her.

There are divorced men and women who behaved badly in past relationships, but there are divorced men and women who are wonderful people who, for complicated and personal reasons, decided that the best option for their children’s well-being and their own mental health was to divorce. Sometimes divorce is unavoidable. Instead of judging him for being divorced, we can look at how he has handled himself during and after the divorce: How involved a father is he? What is his relationship like with his ex-wife? How does he speak to and about his ex-wife? What does she have to say about him? Your guy seems to be doing a great job.

The second thought of hers that concerns me is her notion that it is “not fair” that you, a woman who has never been married, should have to settle for a man who has been married and has a child. I wonder what it has to do with “fair.” Some might say a divorced man who has shown he can commit and is raising a child well is a great catch. Her feelings are a result of her life experiences. Good news–she doesn’t have to marry him!

The behavior that baffles me is her refusal to go to dinner with you and your boyfriend. Either she knows something and isn’t revealing it to you, or she is letting her own personal agenda come before your feelings. I am sure your friend is a wonderful person. Though we can wonder if she is subconsciously trying to sabotage you, I wonder how she is feeling about your moving on while she remains single. Is she worried about losing you and the intimacy that close girlfriends share? You are about to get married and she may feel she will be left behind. This may be incredibly difficult for her. Your relationship will not be the same.

If you continue on this way, with your friend planting seeds of doubt, be aware that allowing someone in your life who actively criticizes your spouse will ultimately come between you and your spouse. You can talk to your friend, and say something to the effect of: “If there is something specific you know about my boyfriend, please tell me. I would like to know. If you have nothing to report, I need you to stop bringing up his past. This is who I choose. I am OK with him being divorced and having a child. I would like to have you in my life and play an important role in my wedding and future, but on these terms.”

Your job is not to get your friend on board, but to create boundaries in how you allow her on board. You worry so much about her and her feelings, but have you given any thought to yours? How do you feel when she insults your boyfriend and picks apart your relationship? Do you feel hurt by her? Do you want to tell her to take a hike? What are your boundaries? What will you allow her or anyone else in your life to say about your husband?

Stop worrying about what she thinks, and start worrying about what you think. As a married person in a healthy relationship, your first allegiance will be to your spouse, not your best friend. Hopefully your friend has her “aha moment” and stops this. Sometimes people do not act like themselves when a close friend gets married. If she doesn’t change her ways before your wedding, you are going to have to juggle the incredible high of getting married with the incredible low of not having your best friend by your side.

Just a thought: Would you consider seeing a therapist or coach, or speaking to a rav with your friend? Distancing yourself from your friend right now is a reasonable choice. But if you feel that your friend’s behavior is out of character, or that maybe she is not handling your upcoming engagement well, perhaps it would behoove the two of you to seek out an objective party to attempt to get to the bottom of this and help the two of you communicate your feelings and intentions.

Wishing you the best!



Jennifer Mann is presently working as a psychotherapist at Ohel. She also works as a relationship coach and can be reached at 718-908-0512.


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