Without meeting you or your daughter, it is difficult to give advice. However, I can mention several points worth bearing in mind.
Firstly, there is a difference between encouragement and pushing. No one should ever be pushed, but they may need encouragement. It is of utmost importance for you to have a deep understanding of the middos and family of your daughter’s dating partner. You need to know and respect the boy, and feel a sense of comfort and security with your child marrying him. If you do feel that this is a good opportunity for your daughter, and that she is frightened only due to her own lack of experience, then you can certainly encourage her. At the same time, let her know that whatever decision she makes, your love and respect for her will not be diminished whatsoever. Don’t push: once someone is pushed they may never get their balance back.
Secondly, it’s important to differentiate between a clear definable aspect of the dating partner which bothers the individual and the common refrain of, “I just don’t have any feelings for him.” There is a stark difference between seeing a troublesome middah— a bad temper, impatience, disrespect towards parents, always taking on the cell phone even when together with others — and not feeling deep connection. A bad middah is a red flag for the future. A lack of deep connection is normal.
We often confuse the celebrity and excitement of dating and engagement with the deeper human feelings that emerge in a relationship over years. We want things to be exciting. But a tree — and a marriage — takes time to grow, and it’s not exciting. It takes years to build a deep meaningful relationship with another person. That comes from accepting the good moments gratefully and the bad moments gracefully. A couple connects by living a life together and sharing the moments that are the warp and weft of one’s life, not by sitting in a hotel lobby. To expect those feelings earlier is unrealistic.
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