Dear Dr. Chani,

I am dating a guy named Yaakov who I really like, yet I feel that I am in the shadow of a girl who he dated previously. I am wondering if I should look past this issue or if it is a strong enough concern for me to break up with him.

Before I started dating Yaakov, I had heard that he had seriously dated a girl named Sara. It sounded to me like he was ready to get engaged to Sara but she turned him down. When Yaakov was suggested to me, the person who set us up told me that since he had broken up a few months earlier, Yaakov had already moved past it. I heard that Yaakov was a great guy so I agreed to go out with him.

Yet, I suspect that Yaakov is still emotionally attached to Sara. It is obvious to me that he still thinks about Sara and cares a lot about her. When we are on dates and I discuss something about myself, such as my hobbies or my personality, it seems to me that Yaakov is checking off boxes in his head to see how I match up to Sara. For example, I once mentioned that I like to exercise and stay active in my spare time. Yaakov said, “That’s nice, do you also bake?” I happen to know that Sara is an excellent baker and makes custom cookies, so I was somewhat offended by his comment. I felt that he was hoping that I shared a lot of her qualities.

Another time, we were describing our travel experiences and he mentioned that he knew someone who went to an exotic South American country. He described some of the details that he had heard about the trip. From the look on his face, it seemed to me that he was recalling a conversation that he had with Sara.

I feel uncomfortable with dating someone who still has an attachment to another girl. How can he value me for who I am if he is constantly comparing me to another person? How can we have our own relationship if he is still stuck in another one? I would really appreciate your advice on this issue.

Sincerely,
Leah

Dear Leah,

It must have been challenging to start dating Yaakov knowing that he had been almost engaged to another girl a few months earlier. You entered your relationship with Yaakov hoping that he would be emotionally past this experience. You were prepared to give Yaakov a chance, knowing that he had wonderful qualities. Unfortunately, now you are disappointed that Yaakov seems to be thinking about Sara while he is on dates with you. Let’s explore how you can deal with this situation.

It makes sense that you are concerned about Yaakov feeling emotionally attached to Sara and comparing you to her. You would like him to start afresh and appreciate you as your own person — not as a stand-in for Sara. It is unclear to you what Yaakov is experiencing and how this will play out. Will he be able to forget about Sara or will she remain emblazoned on his mind and heart as your relationship with him progresses?

A helpful way to think of this can be as a period of transition for Yaakov. It seems natural for him to still have some thoughts remaining of a person who he was ready to marry. He is only human. Since you enjoy Yaakov’s personality and see that there is a potential for you to have a happy relationship with him, you might choose to proceed as if this issue did not exist. It might make sense to see where your relationship with him goes.

If you put your concerns on the “back burner” and give Yaakov the opportunity to adapt to the new relationship with you, he may be able to let go of his thoughts and feelings about Sara as he forms a new secure attachment to you. While it might be challenging for you to ignore this issue, right now it may be the best approach for you to truly give your relationship a chance. Instead, focus on getting to know Yaakov and allowing Yaakov to get to know you.

If you would like to encourage yourself to put these nagging thoughts you have about his attachment to Sara aside, it might be interesting to think about what would have happened had you not known that Yaakov had a previous relationship. Would it have occurred to you that Yaakov might be measuring you by Sara’s standard? Would you have picked up on the subtleties of how he asked you questions and what he said that seemed to hint to Sara?

Your conversations with Yaakov may be triggering memories that he had with Sara. Still, the emotional impact that this has on you might be greater because you were prepared for this possibility and were looking out for it from beforehand. Being aware of preconceived notions you had going into your relationship may help you to take his comments in stride and not get as concerned by them.

On the other hand, if you keep on dating and continue to feel that Yaakov is comparing you to Sara and cannot seem to “get over her,” it might be helpful to have a conversation with Yaakov about it. Start by conveying to Yaakov a few specific personality traits that you like about him. Let him know that you appreciate him and that you think your relationship has potential. Then, explain to him that “at the same time,” you are getting the impression that he compares you to Sara. Give him some examples and ask him if he can be more aware of this tendency. Express to him how it makes you feel when you sense that he is thinking about Sara on your dates with him. You can tell him that you feel inadequate or uncomfortable when he measures you against a standard that he seems to have set for himself based on Sara. Ask him to try to appreciate you for who you are, without assessing what qualities you and Sara share.

After you have communicated how you feel, ask Yaakov what he thinks about what you have said. Give him a chance to reflect and respond to you. If your conversation goes smoothly, hopefully this will sensitize Yaakov to the issue and his new awareness will help him to let go of Sara’s image and focus on your unique qualities. However, if your concerns remain, it might be helpful for Yaakov to discuss his feelings with a professional. It also might be advisable for you to let Yaakov know that you are unable to continue. Instead, look for a person who will value you and feel blessed to have found you.

Wishing you much success and a Chag Kasher V’Sameach,

Chani

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Dr. Chani Maybruch is a social psychologist who has specialized in helping people build and enhance their relationships for over two decades. If you would like to improve your relationship with yourself, your loved ones or others in your life, reach out to her at chanimaybruch.com.