Breaking Up is Hard to Do; 4 Scripts to Help you Through It

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As the song goes, breaking up is hard to do. It’s hard irrespective of the method of delivery: in person, on the phone, by text, or via e-mail. It’s hard irrespective of the length of the relationship – or pre-relationship. Yes, it’s even hard to “break up” after a first phone call with someone who wants to meet you in person.

Ok, maybe breaking up after one phone conversation isn’t technically a break-up. However, if you’re engaged in online and meet-in-person dating, you’re going to come to various relationship-ending crossroads not only after you have been dating someone for awhile but sometimes at the very beginning of establishing contact.

For the purposes of today’s conversation, a break-up is defined as cutting off a relationship after a phone call, a first date, 2 or 3 dates, or a several-month relationship. And the focus of this conversation is what to say and how to say it when you’re the one instigating the break-up.

Since today is Pi Day, let’s have some vegetable quiche while we talk about breaking up when you’re the initiator.

For me, the difficulty with this whole process is my hesitation to hurt someone’s feelings. I don’t want to look into someone’s eyes (or have to avert my gaze) while telling him I don’t want to see him anymore. My brother thinks it’s safer to not turn down a “new” guy in person since he could get angry and I don’t really know how he handles anger. I hadn’t thought of that and it makes me feel like less of a difficult-moments coward.

I recall two first dates where I actually had the balls to say there would likely not be a second date. In both cases, the guys were so over-the-top strange that I felt less anxious about hurting their feelings. I hedged when they asked about going out again and said, “Perhaps. I need to think about it.”

Guy A asked me to rate him and our Starbucks date after 10 minutes! Guy B couldn’t stop approaching strangers to gab while we were strolling down the street and then proceeded to tell me about— and show me pictures of — the nude beaches he liked to frequent. Sigh. So, you can see why I was less worried about their reactions.

If there’s really nothing wrong with a guy, but I’m just not interested in him, then I find it easier to email him my rejection after the date. If a man hasn’t asked me out for date #2, but it’s clear he wants to see me again, I’m proactive and let him know where I stand. Otherwise, I wait until he asks me out before delivering this last message.

My response expresses my feelings about the fledging relationship in terms of two key components of romance: chemistry and connection. No one can deny these are important and that the lack of these essential ingredients means it’s time to hit the delete button. Chemistry and connection can also be used in your script when you don’t want to meet a man you just had a 2-hour phone conversation with.

If you’re breaking up with a guy you have been dating for 2, 3, or 4 months, you’ll need to be more specific about why the relationship is not working for you.

4 Break-up Scripts: What to Say or Write in a Nice Way

Adjust the phrasing of the following “scripts” as needed to match your style and comfort level and to incorporate any relevant details about your relationship. These explanations were emailed to the men in question. If you’re going to speak them over the phone, they may need personalization so the phrasing sounds natural for you.

  • After emails and a phone call: Hi his name, Although I enjoyed our conversation, I came to realize we are not a match. After doing the online thing for awhile, I’ve gotten pretty good at figuring out early on who I will click with in a relationship. So sorry about this and I wish you luck in finding “the one.”
  • After 1 date: Thank you for a nice lunch  I’m sorry to say I did not feel the connection or chemistry I am looking for.  I certainly was hoping for it and you are a very nice guy – and a good hugger.  Well I wish you luck in finding your match. Take care, your name.
  • After 2 or 3 dates: You know I try to be a straight shooter. I want you to know that I think you’re a very nice guy but I’m afraid I’m not feeling the chemistry that I am looking for in a relationship. I wish you good luck and hope you find what you’re looking for. I am so sorry about this.
  • After 2 to 4 months: Although we have had some very good times, I am starting to feel some distance from you. I’m afraid that I’m no longer feeling the connection the way I would like to. BE SPECIFIC ABOUT WHAT IS NOT WORKING BETWEEN THE TWO OF YOU (e.g., lack of communication, lifestyles are too different, he has no time for you, etc., etc.) END WITH A POSITIVE NOTE IF POSSIBLE.

I wish I had some more bullet points in this list and suggestions for how to break up after a year or two, but I haven’t made it that far in any of my post-marriage relationships. As far as my marriage goes, I did not initiate the breakup so I can’t speak from the dumper’s perspective.

Final Words

Sometimes you don’t need to say anything to your no-longer-a-possibility guy. The relationship just fades away. Hearts beat slower. Conversations get shorter. Emails are sent less frequently. Then, one day, you’re looking through profiles again.

Hey, it’s Saturday night; I can be morose if I want to. Oh, yeah, I do have a date Monday night.


Ciao until next week,





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