June 24, 2018

No is Not a Bad Word: How to Say No to a Second Date


When my client Amy met Justin through an online dating site, it was a happy moment. He appeared to have everything Amy was looking for in a relationship, and prior to their first meeting, she was very optimistic and excited. After a few preliminary emails, they met face to face for coffee and a short intro meeting. Although Amy’s first impression was tepid, she was curious. After all, he looked perfect on paper. She decided to accept a dinner invitation from him.

They went to a nice Italian restaurant and enjoyed a lovely meal with pleasant conversation. Justin was a lovely guy, buy Amy just wasn’t feeling the spark. No zip. No little frisson of possibility. Nothing. When it was time to say goodnight, she dreaded the awkward moment… and how she could exit graciously.

Amy was worried that in order to extricate herself she would have to be hurtful or inconsiderate. She put the decision off by asking Justin to give her a call. She wanted to think about how to proceed, and hadn’t really thought about it beforehand. When she called me for help, the first thing I told her was that saying “yes” when you are feeling “no” is what’s unkind. Honesty may sting briefly but cannot cause the deeper hurt that inauthenticity inevitably will.

Amy and I went on to work through some strategies that may be helpful to you.

  • Be honest. Speaking your truth will be appreciated. No one wants to be pitied, patronized, or strung along. Would you? So try something like this: “I’ve enjoyed the time we have spent together, but I didn’t feel that necessary click to move things forward.” Or: “Thank you for the interesting conversation and the lovely meal. You are really a great person, but I think we are not a match.” And stop there. Do not be pulled into a conversation where you deconstruct the date and have to point out what you felt was missing. That would hurt.
  • Be crystal clear. Sometimes when we think we are conveying information, it turns out we aren’t. Why is that? We are so careful to couch the truth in “thoughtful” euphemisms, that the person we’re talking to is either totally confused, or has a choice about how to interpret what we said. When that happens, people hear what they want to hear. Do not fall into this trap. Your truth must be absolutely unmistakable. Whatever you do, do not lead him or her on and then pull a disappearing act by not answering texts, emails or phone calls. If you have ever been “blown off” or ignored by someone you know how difficult that can be.
  • Be firm. In addition to clarity, be firm, assertive, and immovable. Once you have set your boundary do not allow yourself to be badgered into accepting a second date. Trust yourself enough to know what is best for you and move on to find your ideal match. If your date continues to bring up possibilities, and what ifs, and tries to bargain with you, simply repeat what you have said, word for word. “I’m sorry but I do not think a second date is a good idea.” Or, “I am glad I met you but we won’t be seeing each other again.” This is the “broken record technique” and works well here. No means no. Eventually the message will get through.

Red flags to look out for in this situation:

  • Fear—Fear often motivates us to do things we know at a gut level are wrong for us, or to fail to do things we know are right. How might that look when considering a second date? “What if this is my last chance to find a decent guy/gal?” would be a fear reaction. DO NOT act out of fear. It is a weak position and does not do justice to how wonderful you are.
  • Insecurity—Like fear, insecurity undermines your best self. Insecurity might whisper in your ear: “What if I can’t do better?” Silence that insidious whisper and know that you can and will find the right person. “Settling” does a terrible injustice to you… AND the other person!

When you show up at a first date, even if you are as optimistic as can be, it’s a good idea to have some solid strategies in your hip pocket in case you need to bow out gracefully. Hope for the best but be prepared for the worst is a decent rule of thumb. Saying no to what you don’t want frees up space for what you do want in your life and relationships. Don’t waste another minute—go for what you want and get the love you deserve!


  1. Hi, I read your blog like every week. Your writing style is witty, keep it up!

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