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Dear Dating Coach,

A year ago I met a great guy at a meal that someone hosted for singles. We quickly started dating and things were going well. After months of dating, we finally discussed our future, but he was not ready, so we just continued to date. Since then, every couple of months we seem to have the same conversation, and he is never ready. His parents got divorced and he always says that he needs to be sure that this is “right” before walking down the aisle. We have spoken to my Rebbetzin, his Rav, and a therapist together and he refuses to be “pressured.” I want to marry him, but at this point I don’t know what to do. How do I get him to see that this is “right?!”


Marry Me


Dear Marry,

A few years ago, we lost a palm tree to a hurricane. The tree was completely uprooted by the strong winds and left a hole in our front lawn. At first, we tried to simply walk around the hole, but it became a tripping hazard in the morning rush to the car. Then we tried to fill it with dirt, but no matter how much soil we added, it never seems to be level with the rest of the grass. Then we tried mulch, but the look was off and didn’t go with the grass. Finally, we tried new sod, but there is still a slight dip where our dear palm once stood. At this point, we accept that the dip is here to stay. So, if anyone has a palm tree that they don’t need…


Accept What Is…

It’s exciting to meet someone in a seemingly simple way. You went to a meal, connected, and started dating. The organic connection was a gift and you were not going to let it pass you by. You put effort and care into nurturing a bond between the two of you and after a few months you were sure that this was the person you wanted to marry. But he wasn’t. So, you gave him time, and then a bit more time, and then a bit more. You want this to work, but you don’t know what to do to make him commit to you.


Let Go of What Was…

Please forgive me. I know that you have put tremendous effort into this relationship. You were supportive and caring. You reached out for guidance and have been very patient. But I have said this before and I will say it again; if someone cannot commit to you after a year, they are unlikely to commit to you ever. It is time to walk away. I know this is hard and do not discount the emotional investment you have made. But at this point, there is nothing YOU can do to change how he feels.


Have Faith in What Will Be.

This is not an ultimatum or a way to pressure him in any way. This is you realizing that you can only control your feelings and actions and not his. He doesn’t want to marry you. You have given him a year, and this is enough. End things kindly and with compassion and feel confident in the effort that you put into building a future together. Ultimately, this is how he feels, and acceptance, though very difficult, is a must. Hashem should bless you this Shavuos and give you strength to heal and meet the right person for you.


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Henni Halberstam is a Dating and Marriage Coach whose expert advice will help you navigate dating and relationships in order to ensure a successful marriage. You can contact her at [email protected] to schedule a phone session.