One hope that we all share when about to go out on a date – whether it’s a first date or a tenth date – is wanting to have a good time. Everyone wants to have fun on a date. It’s painful to sit through a date where you’re either bored to death or you’re sitting there trying to pull teeth in order to have a simple conversation to get to know him/her, not even trying and sitting and embracing the awkward silence.

Expectations grow from there. Once you have fun with someone for a date or two or three, you hope that the fun continues and the relationship turns serious. It’s only reasonable to buckle down after a while and have the “serious discussions,” to see if the relationship can be one that helps you build your bayis ne’eman b’Yisrael or not. Here is a letter from a woman who has had a good time with whom she is dating, but she can’t get him to sit down to have the “serious discussion,” and doesn’t know what to do.


Dear Goldy:

I have dated Avi (not real name) longer than I have dated anyone before. We click. I am having the most fun I have ever had dating. But that’s the thing: We’re having too much fun and not enough serious conversation.

Avi is a jokester/prankster. He’s the fun-time guy with his friends, and he described himself as being the class clown in high school...all that. And I can see it. But now I want him to get serious. Life isn’t just fun. I need to make sure that not only our personalities match, but we want the same things out of life, what his hashkafah is, and what he hopes for it to be as he ages. Every time I try to start the conversation, Avi makes a joke or changes the topic. I told him that I wasn’t trying to have the “break up” talk with him; I just want to get to know the real Avi better. In a nutshell, he said that what I see is what I get; he isn’t a complicated person. Great, but we still need to speak – or at least I do.

I don’t get the impression Avi dates “for fun” or jumps from girl to girl. All I know about him is what the shadchan told me (and the references I called). He talks about his family and friends, but never anything deeper than that.

What can I do? Any ideas?

Cindy (my real name)


Thanks for your letter, Cindy.

You seem to have overcome the first hurdle of dating: finding someone you click with. Now you need to know if the click is a permanent one or temporary. I don’t know how long the two of you have been dating, since you didn’t write it, but could it be that while you think it’s been enough of the “fun times” and now it’s “serious time,” that Avi feels differently? As I’ve always written, there’s no dating rule that by date number five or nine you have to have “the talk” and then make a decision. While it’s not wrong if you feel like fun time is over, Avi still may be in his fun stage, wanting to get a better picture of your personality and who you are.

I’m going to say that you have the patience of a parent teaching a 16-year-old how to drive. If it were me, and the one I was dating never wanted to get serious for a few minutes, I’d shake him or try to knock some sense into him. As I told my daughter the other day when she said she was “Booorrrreeeedddd” after five minutes of turning off my tablet: “Life is sometimes boring.” It isn’t all fun and games, and we have to take the boring with the fun, too. Sometimes “adulting” isn’t fun. That’s what Avi needs to learn.

It was smart thinking on your part for prefacing the discussion by telling him you weren’t having the “break-up” talk and only want to get to know him. Guys and girls both hate when the person they are dating says, “We need to talk...” or something like that. But to shut the conversation down completely? Hmm.

People have their own definitions of fun, and their definitions may differ from one person to another. I am wondering if your “fun times” is sitting in lounges or going out to eat or a long walk together, or if it’s going to a gaming arcade, bowling, taking a cooking class together. Are you sharing experiences, or just having fun by enjoying each other’s company? Nothing is wrong with either, but that would also help for me to better understand some of the fun and part of Avi’s character. Either way, having fun is a great way to begin a relationship.

At some point, things have to get serious; questions have to be asked and disclosures about important information may have to be said. Dating isn’t just about fun; it’s about exploring each other’s personality, finding out what they want from life, what their 5/10/15-year plan is, etc. Frumkeit comes into play here.  Currently, all you know is Avi’s stats and that he is a fun guy. But I’m sure he has mentioned something that would give you more insight into who he is. You can’t be dating someone for “a while” and not know anything about him. He may have causally said something, and you may not have picked up on it because you weren’t in “serious” mode. Some may say, “Let’s just get this stuff out of the way...” and go through a list of topics/questions and that’s that. But you don’t seem to be able to get Avi to do that. But I can understand when Avi said that what you see is what you get. He probably doesn’t think of himself as too complicated, easy going, so no need to look/ask for trouble.

Do you know if Avi has been in any serious relationship before and may have had his heart broken, which can be why he doesn’t want to get serious yet? What type of job does Avi have? Is it one that matches his personality (maybe an event planner), or one that is serious, and it takes a toll on him because he can’t show his personality at work – maybe a specific type of lawyer, or working for an agency that helps the abused? Then I can understand why Avi has that need to be fun; when things are intense at work, you need to let loose in your free time.

Have you or anyone asked Avi the all-important question: Does he even want to get married? It may sound funny, but some guys (and even some ladies) like their life the way it is and like dating different people. I distinctly remember my father and I standing together at a simchah, and he pointed someone out to me and said, “You see him? He ran in the same group as I did, but he never settled down. He dated everyone, liked having someone on his arm, or even someone on each arm to walk around with.” The man he was referring to was about the same age as my father, was good-looking, laughing with someone at that moment. I asked my father if he knew back then that this man was never going to settle down. My father said that when friends started to get married and settled with children, he said he considered himself lucky to still be single.  My father didn’t exactly describe this man as a player. He genuinely liked the women he dated, but he also liked being single and not being tied down. I am not saying Avi is like that, but there are people like that.

Did you speak with the shadchan about this? Even if you are past using the shadchan who redt the shidduch, the shadchan may be the best one to ask. He/she knows Avi for some time, and shadchanim are used to talking with singles about the “serious stuff.” If you’re using one of the shadchanim I refer to highly, who know what they are doing, call and tell him/her you are at this point and need help to figure out how to get through this. I’m sure he or she will readily help you, since you don’t seem to be making any headway on your own.

Yup, dating’s tough. Even if you find the right one, things aren’t always as smooth as you would think. Hatzlachah to you all!

Goldy Krantz  is an LMSW and a lifelong Queens resident, guest lecturer, and author of the shidduch dating book, The Best of My Worst and children’s book Where Has Zaidy Gone? She can be contacted at This email address is being protected from spambots. You need JavaScript enabled to view it..