It’s not uncommon for couples to go out a time or two (or more), and then one of them calls it quits because he/she isn’t feeling it. Months or years pass, and they rethink the situation and are able to arrange to go out with the person they ended it with again. Many times, the second time around ends with a happily ever after.
It wasn’t the right time the first time around, but now, the time is right, and so a simcha is made and two lives are blended into one. But sometimes the second time around doesn’t end so happily, and that’s okay. In this letter, I think someone thought that this was going to be one of those happily ever after endings.
Dear Goldy,
I went out with Yaakov last year. He’s a nice guy, but after a few dates, I wasn’t feeling it. I wasn’t excited or feeling butterflies when I thought of him or going out with him. I ended up breaking up with him. Is it even called “breaking up” if we went out four or five times? We weren’t boyfriend/girlfriend.
I got to thinking a few months ago about whether there was anyone I had gone out with in the past, whom I had been the one to end things with, who maybe I could give another chance to, if he wasn’t married yet and was willing to try again. I thought of Yaakov and one other guy. I’m a little older, wiser, and more experienced in life now, and maybe my mind is in a different place than it was when I first dated the other guy and Yaakov. I called the shadchan who set us up, but the first guy had gotten married. I called the other shadchan who had redt the shidduch with Yaakov. She made a call, and Yaakov was willing to try again.
So far, Yaakov and I have been out four times. I’m trying, but I still can’t seem to develop feelings toward Yaakov. He’s nice, has a good personality, and is good-looking, but I’m not feeling any type of connection. I told myself that I’ll keep going out with him (if he wants to) until there is a concrete reason that tells me I need to end it. I’m really trying to be open to everything, giving him a chance, asking myself what I feel are important questions, seeing where I can get what I want, if I’m compromising or if I’m settling in some areas… Unless something very different happens, I may just have to end it because there is “no connection.” I can’t force it. And at this point, I should be feeling something, right? But I’ll give it another date or two.
My worry is that Yaakov sees this second time as “our time.” He even called this our “b’shah tovah.” As soon as he said that, my stomach dropped. He told me that it took him time to move on the first time, and because I had ended things, he couldn’t call the shadchan and ask her to call me. He was thrilled when the shadchan called him now about me. This worried me; he’s happy and telling me all of this. He’s letting his guard down, which is good for him, but I’m not there yet. I made my intentions clear: I was revisiting this because I want to make sure I ended things for the right reasons, and in order to do that, we had to go out again, and I had to give him another chance and be open this time. I don’t want to sound conceited, but I had to say something. He was giving me the feeling that he was beyond the “let’s try this out again” point and was in “this is my kallah” territory. I was very clear. I couldn’t tell him that I checked if another guy was still single before I called the shadchan about him. I couldn’t be that mean. But I was honest. I don’t want to mislead him. But Yaakov sort of poo-pooed that and said, “The second time’s usually the charm.” Ahhhhhhhh!
I’m putting that out of my head, but it keeps creeping back in and ruining my attempt to be open and to evaluate what this could turn into. Now I feel pressure because Yaakov clearly sees this ending with us under the chupah. The pressure is getting to me and already making me regret this second-time decision.
Advice?
Leah
Thank you for your letter, Leah.
Yes, I’m very well acquainted with people rethinking their decisions about people they have dated in the past and trying it again. My story is sort of like that because I called it quits with my husband after the first date (for the dumbest reasons. I was overthinking the situation), and then the second time… dating just happened. There was one fellow whom I dated six times (I looked back in my journal). I ended things, and over a year later, like you wrote in your letter, I was older and wiser and thought maybe I had ended things for frivolous reasons, and if he was willing, I wanted to date him again. He said yes. From the get-go, I knew I was in over my head. This time, we got to date #4 when I ended things, and this time, I knew it was for concrete reasons. He was acting just as Yaakov is acting. He had dropped his guard, telling me things I’m sure he hasn’t told many people and being silly at times (nothing is wrong with letting loose and being silly), but I was very much not feeling it.
I also want to say kol hakavod to you for revisiting men you said no to in the past and seeing if the “no” was still an issue or if you have grown, changed priorities… and what bothered you before, you can live with now. Many people don’t revisit past dates. It takes courage to make the call because the person can always say no: “You’re telling me she’s being gracious and letting me date her again? Who is she, a queen? No thank you.” But good for you and all the others who have taken the chance and done that.
At the moment, you aren’t thinking of standing under the chupah with Yaakov yet. But would you stand under the same umbrella he would? I’ve had the uncomfortable situation of being stuck under a date’s large umbrella, even when I had my own. I wasn’t feeling it, and so umbrella sharing was too close for comfort for me in all ways. You wrote that you were honest with Yaakov and said that you’re still exploring your feelings. He may be jumping five steps forward, but that’s on him. As long as you’re honest and don’t mislead anyone about your intentions, then you have nothing to worry about. You may want to repeat your intentions when given the opportunity. Make it clear he shouldn’t be renting a tux yet. I would even go so far as to say how uncomfortable it makes you because I’m sure Yaakov wouldn’t want to scare you away.
You wrote that you’re just trying to be open and evaluate the situation. I’m not loving the word “evaluate” here. Just go with the flow. Have no expectations, so you won’t be disappointed and can always be pleasantly surprised. Just let things happen, and if you see that after a date or two or three more you truly have no feelings for Yaakov, that could be a concrete reason in and of itself. How long must one go out with someone until they begin to have feelings? I know someone who literally went out with her husband 10 times before she said she liked him. Why did she last 10 dates? “Because there was no reason to say no. He was nice. The dates weren’t horrible. But then it happened.” I’m not telling you to hang in there until date 10. You know when it’s been sufficient time for you to feel one way or the other toward him. But if you are feeling pressured by what Yaakov is saying, which is his way of saying he’s having a great time and hopes things work out, you can tell him that you feel pressure when he says that because you’re not there yet, and you’ll let him know when and if you get there. Ask him to keep it light and friendly. No pressure. It’ll benefit him as well because the less he says about it, the more open you are to thinking about him and whether you can have a future with him.
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.. Goldy is an experienced dating coach offering private sessions. To inquire, contact her at This email address is being protected from spambots. You need JavaScript enabled to view it..
