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
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.