2 added info from comments, cleaned up anecdote
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Good thinking to be prepared. If you've decided to tell him after the fact...

Do:

  • Be upfront
  • Be prepared for an angry reaction
  • Maintain your composure
  • Acknowledge and validate his feelings (you say he is a good friend, after all)

Don't:

  • Try to hide what's happening
  • Expect him to forgive you immediately, let (let alone be happy for you)
  • Tell him he's wrong to be upset

Find a time when the two of you can have a conversation. A quiet casual dinner wasn't the worst place to do it, but pick somewhere that you are free to leave whenever (so you/Kyle don't feel trapped, and can leave whenever the conversation indicates).

Give him the short version first: "Kyle, I wanted to let you know that Penny and I are dating." You want to sound respectful of his feelings, but not apologetic for your own actions (which would imply you did think you did something wrong).

Let his reaction guide whatever else you say. He may want more information (e.g. when did this start?) - he may not - he may storm out. Even if he reacts emotionally, stay calm yourself. Raising your voice or responding with anger will only feed into the feeling that this is an attack on him.

He may be concerned that you're going to learn intimate or otherwise private details about him via his relationship with Penny. If you and Penny have any ground rules regarding that, this is a good time to let him know and address those concerns.


My experience:

I was "Kyle" in a situation like this. "Steve" asked me to dinner, which was fairly unusual in the first place, and given how dodgy they'd been lately when "Penny" was mentioned, I had a good guess what was up. They waited until the end of dinner to actually spit it out though, after I started saying "well, good catching up, I should probably get going because work tomorrow..."

"Steve" finally told me then, and I was angry. My thought process was: I felt thatknew they had been hiding it from me for a long time and them dating didn't make any sense, which meant they knew I'd be upset by it, which meant since they did it anyways without talking to me about it, they must not care about me. "Steve's" reaction was to berate me for being upset and remind me that I didn't get a say in who either of them dated. Technically true, yes, but only drove home the feeling that "Steve" didn't actually care how I felt.

This continued overI tried for months of me trying to talk to themit out with "Steve", thinking "maybe they just don't understand why this hurts me?" All I wanted was for them to actually reach out to me and acknowledge that I was hurt and upset by how they handled this. But they never did, and we are no longer on speaking terms. Don't be that Steve!


I realize this might sound a bit dire, but in the best-case scenario where he reacts fine, you can just breathe a sigh of relief and move on with your usual friendship. Just be mindful that - especially with the timelines - he may not have fully processed the breakup yet and may need some space and time to get used to the idea of you two dating.

Good thinking to be prepared. If you've decided to tell him after the fact...

Do:

  • Be upfront
  • Be prepared for an angry reaction
  • Maintain your composure

Don't:

  • Try to hide what's happening
  • Expect him to forgive you immediately, let alone be happy for you
  • Tell him he's wrong to be upset

Find a time when the two of you can have a conversation. A quiet casual dinner wasn't the worst place to do it, but pick somewhere that you are free to leave whenever.

Give him the short version first: "Kyle, I wanted to let you know that Penny and I are dating." You want to sound respectful of his feelings, but not apologetic for your own actions (which would imply you did think you did something wrong).

Let his reaction guide whatever else you say. He may want more information (e.g. when did this start?) - he may not - he may storm out. Even if he reacts emotionally, stay calm yourself. Raising your voice or responding with anger will only feed into the feeling that this is an attack on him.

He may be concerned that you're going to learn intimate or otherwise private details about him via his relationship with Penny. If you and Penny have any ground rules regarding that, this is a good time to let him know and address those concerns.


My experience:

I was "Kyle" in a situation like this. "Steve" asked me to dinner, which was fairly unusual in the first place, and given how dodgy they'd been lately when "Penny" was mentioned I had a good guess. They waited until the end of dinner to actually spit it out though, after I started saying "well, good catching up, I should probably get going because work tomorrow..."

"Steve" finally told me then, and I was angry. I felt that they had been hiding it from me for a long time and them dating didn't make any sense. "Steve's" reaction was to berate me for being upset and remind me that I didn't get a say in who either of them dated. Technically true, yes, but only drove home the feeling that "Steve" didn't actually care how I felt.

This continued over months of me trying to talk to them, thinking "maybe they just don't understand why this hurts me?" All I wanted was for them to actually reach out to me and acknowledge that I was hurt and upset by how they handled this. But they never did, and we are no longer on speaking terms. Don't be that Steve!


I realize this might sound a bit dire, but in the best-case scenario where he reacts fine, you can just breathe a sigh of relief and move on with your usual friendship. Just be mindful that - especially with the timelines - he may not have fully processed the breakup yet and may need some space and time to get used to the idea of you two dating.

Good thinking to be prepared. If you've decided to tell him after the fact...

Do:

  • Be upfront
  • Be prepared for an angry reaction
  • Maintain your composure
  • Acknowledge and validate his feelings (you say he is a good friend, after all)

Don't:

  • Try to hide what's happening
  • Expect him to forgive you immediately (let alone be happy for you)
  • Tell him he's wrong to be upset

Find a time when the two of you can have a conversation. A quiet casual dinner wasn't the worst place to do it, but pick somewhere that you are free to leave whenever (so you/Kyle don't feel trapped, and can leave whenever the conversation indicates).

Give him the short version first: "Kyle, I wanted to let you know that Penny and I are dating." You want to sound respectful of his feelings, but not apologetic for your own actions (which would imply you did think you did something wrong).

Let his reaction guide whatever else you say. He may want more information (e.g. when did this start?) - he may not - he may storm out. Even if he reacts emotionally, stay calm yourself. Raising your voice or responding with anger will only feed into the feeling that this is an attack on him.

He may be concerned that you're going to learn intimate or otherwise private details about him via his relationship with Penny. If you and Penny have any ground rules regarding that, this is a good time to let him know and address those concerns.


My experience:

I was "Kyle" in a situation like this. "Steve" asked me to dinner, which was fairly unusual in the first place, and given how dodgy they'd been lately when "Penny" was mentioned, I had a good guess what was up. They waited until the end of dinner to actually spit it out though, after I started saying "well, good catching up, I should probably get going because work tomorrow..."

"Steve" finally told me then, and I was angry. My thought process was: I knew they had been hiding it from me, which meant they knew I'd be upset by it, which meant since they did it anyways without talking to me about it, they must not care about me. "Steve's" reaction was to berate me for being upset and remind me that I didn't get a say in who either of them dated. Technically true, yes, but only drove home the feeling that "Steve" didn't actually care how I felt.

I tried for months to talk it out with "Steve", thinking "maybe they just don't understand why this hurts me?" All I wanted was for them to actually reach out to me and acknowledge that I was hurt and upset by how they handled this. But they never did, and we are no longer on speaking terms. Don't be that Steve!


I realize this might sound a bit dire, but in the best-case scenario where he reacts fine, you can just breathe a sigh of relief and move on with your usual friendship. Just be mindful that - especially with the timelines - he may not have fully processed the breakup yet and may need some space and time to get used to the idea of you two dating.

1
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Good thinking to be prepared. If you've decided to tell him after the fact...

Do:

  • Be upfront
  • Be prepared for an angry reaction
  • Maintain your composure

Don't:

  • Try to hide what's happening
  • Expect him to forgive you immediately, let alone be happy for you
  • Tell him he's wrong to be upset

Find a time when the two of you can have a conversation. A quiet casual dinner wasn't the worst place to do it, but pick somewhere that you are free to leave whenever.

Give him the short version first: "Kyle, I wanted to let you know that Penny and I are dating." You want to sound respectful of his feelings, but not apologetic for your own actions (which would imply you did think you did something wrong).

Let his reaction guide whatever else you say. He may want more information (e.g. when did this start?) - he may not - he may storm out. Even if he reacts emotionally, stay calm yourself. Raising your voice or responding with anger will only feed into the feeling that this is an attack on him.

He may be concerned that you're going to learn intimate or otherwise private details about him via his relationship with Penny. If you and Penny have any ground rules regarding that, this is a good time to let him know and address those concerns.


My experience:

I was "Kyle" in a situation like this. "Steve" asked me to dinner, which was fairly unusual in the first place, and given how dodgy they'd been lately when "Penny" was mentioned I had a good guess. They waited until the end of dinner to actually spit it out though, after I started saying "well, good catching up, I should probably get going because work tomorrow..."

"Steve" finally told me then, and I was angry. I felt that they had been hiding it from me for a long time and them dating didn't make any sense. "Steve's" reaction was to berate me for being upset and remind me that I didn't get a say in who either of them dated. Technically true, yes, but only drove home the feeling that "Steve" didn't actually care how I felt.

This continued over months of me trying to talk to them, thinking "maybe they just don't understand why this hurts me?" All I wanted was for them to actually reach out to me and acknowledge that I was hurt and upset by how they handled this. But they never did, and we are no longer on speaking terms. Don't be that Steve!


I realize this might sound a bit dire, but in the best-case scenario where he reacts fine, you can just breathe a sigh of relief and move on with your usual friendship. Just be mindful that - especially with the timelines - he may not have fully processed the breakup yet and may need some space and time to get used to the idea of you two dating.