Dear Matchmaker Rabbi:

One of my biggest problems when it comes to my dating life is taking things too quickly. When I fall, I fall hard and might scare girls off.  The problem is I feel like I have to act fast because, in the past, I have waited too long to ask out a girl I liked, and she found someone else.

I guess what I am asking is what pace to go? I feel like either way, I lose in the end. I am frustrated and hoping to improve my dating life.

— Rushing Into Things

Dear Rushing Into Things:

You’re right that timing can be tricky, and I don’t think there is a magic rule to follow. I also think it depends on where this dating is happening. If it’s through a dating site or singles event, people are going to expect you to “ask faster” because you are both there with the clear intention of finding a date. If you are meeting through social circles, or a work or social club, you might need to “test the waters” more cautiously to gauge whether the person is even looking for a relationship (let alone might be interested in you in particular).

It sounds like, regardless of the venue, you tend to err on the side of too much caution. My advice, then, is to be a bit bolder. If you meet someone who excites you, simply ask her in a casual but clear way: “Hey, would you like to get a coffee sometime?” Make sure that the outing you suggest can’t be confused with the kind of invite you would ask a platonic friend.

That said, there is a difference between being direct about your romantic interest, and showing a level of interest that is inappropriate for how well you know each other. I know I always felt weary of a guy who came on too strong, too fast. This is because I knew his interest was built on his projected assumptions about me, or because he thought I was “attractive” or “bubbly,” rather than on deeper qualities of who I am as a person. How much can a person really like you, after all, before they really know you?

Until two people have taken the time to simply “hang out,” and share their life stories and dreams, its hormones talking, not relationship material.

— The Matchmaker Rabbi

To ask The Matchmaker Rabbi a question, please email

Joysa Winter, aka The Matchmaker Rabbi, knows all about how hard it is to find lasting love. It took her 17 years to find Mr. Not Wrong! In that time, she tried just about every singles site, dating club and Matzah Ball known to humanity. Now in her fourth year of rabbinical school and the mother of 1.5 kids, nothing brings her greater joy than officiating a wedding. She is finishing a book on her dating adventures called Chasing Cupid, Tales of Dating Disaster in Jewish Suburbia. You can follow her on Twitter at @wanderinghebrew.

  1. I just went on a date with someone. And I fell quick and hard. I guess i like to take things slow and he wanted a kiss… when i just met him. Long story short, i had a door in my face, and a long crying ride home. Should i drop my morals of taking things slow to meet the pace of the person I’m dating or stick to my morals?

  2. How fast to go? That’s a question to which there is no answer. For some reason, women seem to think that a man should just know this. And, for most women, they have no idea what they want themselves.

    Of course, women want someone who is interested in touching them, but they know a few things about being physical and the male brain. First of all, if they are aggressive, they might scare the guy away. Second, if they let him do something, they establish a high water mark, and that activitiy is now on the menu going forward. Third, if they are too easy, he might loose interest. Forth, they can get STDs or preggers. So, the usual result is playing hard to get.

    A woman’s sex organ is between her ears. You cannot get anywhere physically with a woman unless you connect emotionally, but I think you understand that. So, if you feel an emotional connection and wait too many dates to kiss and hug her, she’ll think you are not interested. So, step up to the plate.

    My advice is to get in touch with your senses. Observe her posture and her vocal tone and rate, her eyes, her lips, and her skin tone. When you feel the connection, lean in slowlly and kiss her gently. If she pulls back, then you’ll get the message. Nothing ventured, nothing gained.

  3. Dating in the U.S. has been incredibly frustrating to me. Even after going out for months, I never know where I stand with a particular woman. I’m very loyal, very nice, but it seems that a huge majority of American women are ice cold and do not care. Even when they say “I love you”, it seems to be purely rhetorical. And having had sex does not seem to improve a relationship either. There is not warmth, no real feeling of friendship. After spending an entire weekend together, there is no tenderness … when we say goodbye, it is like saying goodbye to my real estate agent. Dating here .. it’s giving me headaches and stomach ulcers. Small wonder that there are so many divorces in this country. I wonder how successful relationships are even possible…….

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