Jewish Dating Advice: How to ‘Break Up’ After a Few Dates

by Sandy Weiner, Dating Coach, Last First Date

You realize your date is not a good fit for you after one or two dates. How do you ‘break up’? While I usually recommend going on at least two dates with most people, sometimes there are red flags after only one date. You know that person isn’t right for you, but it can be uncomfortable to tell your date you’re not interested. You don’t want to hurt their feelings.

Do you pull a disappearing act and never speak to them again? Or do you lie and say you’ve rekindled a relationship with an old flame?

There’s a better way to say goodbye.

Of course you don’t want to hurt your date’s feelings. I agree; we should treat everyone with kindness.

But I also believe we should strive to be truthful. Here’s how to end things with kindness and honesty, whether it’s after one date or a few.

I’ll illustrate with a story.

‘Sara’ was supposed to have a coffee date with a new man she met online. He called to cancel that afternoon. “My new iPhone broke today”, he said, “So, I have to cancel our date”.

“What does a broken phone have to do with meeting for coffee?” she thought. She was concerned that he might be an anxious guy who doesn’t do well in a crisis, which is a deal breaker for her.

But, she didn’t want to read too much into things before meeting him. So, she agreed to reschedule for the following week.

The first date

He greeted her outside Starbucks, and as they walked in, he told her he doesn’t drink coffee or tea. “That’s a bit strange,” thought Sara. “Why did he ask me to meet him at a coffee shop?” But, she was trying really hard not to judge him, and she took a deep breath and smiled. He ordered lemonade, she an iced latte, and they sat down to talk.

The conversation was a bit awkward at first, but as he relaxed, there was more of a flow.

They even laughed a few times, which is a good sign of connection. They discovered they had friends in common and enjoyed many of the same activities.

He admitted to being nervous, and she knew that first dates are not always a good indicator of a person’s full personality. A second date might bring him out more. So when he asked if she’d see him again, she said yes.

He started texting the next day, and that’s when things started to get weird.

Him: Hi!

Five minutes later…

Him: I found you on Facebook. Such beautiful pictures of you! Now I’m going to be tongue-tied the next time I see you!

Sara: Thanks for the compliment. I saw that you sent me a friend request on Facebook. Nothing personal, but I am not going to accept your request, because I don’t like to be connected on social media with people I date.

(Sara started to feel that he was stalking her.)

Him: Well, that means we are going to date! We both will be speechless on the next date!

That last text made Sara very uncomfortable. He was overly emotive, anxious, and seemed to lack confidence as well.

She had already promised him a second date, but she was certain she didn’t want to see him again.

She wanted to end things kindly and firmly. Here’s what she wrote:

“This is not easy for me to say, and perhaps it won’t be easy for you to hear. I’ve come to the conclusion that it’s best not to continue dating. You seem like a wonderful person with many great qualities. I’m looking for someone who matches with my unique interests, goals and personality in a different way. I certainly hope you can understand. I enjoyed meeting you and wish you the best. I just know I am not the right person for you and want you to find the one that is.”

He immediately wrote back: “I can’t say I’m not disappointed, but I understand. It was very nice meeting you and I wish you nothing but the best. You deserve it.”

Lesson learned: listen to your gut.

Have you ever ignored your wise inner voice, the voice that recognizes red flags? That voice knows what’s best for you. And if it’s telling you that there’s something really off with the person you’re dating, listen closely.

Better to end things right away when the message is loud and clear.

It’s also important to know when to go out again.

Go out on a second or third date if you share common values, you have a similar worldview, and you’re enjoying yourself when you’re together. Do you laugh? Is the conversation interesting? If there are no big red flags, go out again. Often people open up and relax on the second or third date, and that’s when sparks begin to fly.

In Sara’s case, the red flags were there. She dismissed a few yellow flags (canceling a date because of a broken phone, taking her to a coffee shop when he didn’t drink coffee), but couldn’t dismiss the feeling she had after he stalked her on Facebook.

Have you ever ignored your gut feelings about a date and let things progress for too long? Do you find it difficult to know how to end things after a few dates? Please share your thoughts.

About Sandy Weiner

Sandy Weiner, Dating Coach and Chief Love Officer of Last First Date, is devoted to helping women and men achieve healthy, off the charts love in the second half of life. She’s an internationally known dating coach, blogger, radio host, communications expert, and TEDx speaker. Discover the top 3 mistakes midlife daters make (and how to easily turn them around to find a loving partnership). The guide is yours FREE by clicking here.