Dear Rabbi and Shira,

I have gone out with over 50 girls in the last 2 years. I do not consider myself a picky person. I believe that the girl I marry should be both beautiful inside and outside. For some reason, I usually find the girls I go out with to be either one or the other, but not both.
Both of my parents are pushing me to get married. All 4 of my siblings got married by the age of 24 and I'm already 26. I feel like I'm going out almost every week with someone else. Is it healthy to go out so often? Sometimes I feel like I need a break from all this dating.

Guy in Midwood

Dear Guy in Midwood,
Thanks for reaching out. That sounds like a lot of people to have dated. We’d like you to consider who it is that’s setting you up? Do they know you well enough? How on target are the suggestions? Have you reached back out to the shadchan with a response phrased more than, “she’s not my type.” What is your type?
What do you think about your siblings spouses? What are their relationships like? What is your parents relationship like? How do these relationships inform your hopes and fears about who’ll you’ll marry.

You say you don’t consider yourself picky, and then in the same sentence you say that they must be beautiful inside and out, and that you’ve dated 50 women.
 We’d like you to describe to yourself what beautiful inside and out means. If you’re simply rating women on your scale of beauty, like swiping through pictures on your phone, you definitely are not going to see “inner and outer beauty” you are merely seeing an image and are being incredibly unrealistic about life, marriage and its expectations.  Don’t get us wrong, both a chasan and kallah have to be attractive to each other. However, there is a big difference between attractive to each other and objectifying someone as physical traits.  No one is going to be the picture of a baalat-midot-magazine-model in a snapshot at all times and forever. Most people will not fit into their wedding dress or suit forever. Real people are three dimensional, they will grow and change together.  Attraction built on a relationship, will make them always beautiful in your eyes, inside and out. 
So practically, how long are you dating each person? Are you getting to know them, or swiping next? Are you speaking to them about their life and their dreams? Or are you looking for a pretty face who agrees with what you have to say and thinking that it means beautiful inside and out?

Hatzlacha
Rabbi Reuven and Shira Boshnack