How to tell a close friend and partner in business that I'm seeing his ex-girlfriend?

Question

Lets go to the facts first.
Let's call my close friend Bob, and his ex-girlfriend Jane.

Me and Jane go way before I meet Bob. Actually, she presented me to him. Since then, we became really close friends, at the point of starting a business together.

I have known Jane since high school, but never had anything romantically with her. Just friends.

3 or 4 months ago, Jane dumped Bob (they dated for about 8 months), and I was there for him. Stood up for him and went to a lot of places to make him "forget" her. And he did.

Bob knows that we are basically the same, so, the first thing he said to me after the break-up was that "You are free to see Jane if you want to, because you are very much like me."

He probably was sadly mad with her when he said this, and I had no intention whatsoever to go after Jane. But time changes, and after Bob, we started going out, we became closer and now we are going on dates.

I tried to bring up the subject "Jane" to Bob, and he was kinda mad, saying that I would not work with her. (To be clear, I haven't said anything about going on dates with Jane to him).

So, this is a big IF, but a pretty possible one.
If things work it out with me and Jane, I mean, a more serious relationship, I'll have to tell Bob about it. Believe me, having to keep secrecy is not cool.

How should I approach him if it came to be?

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EDIT:

After some time together with Jane, I could clarify in my mind that I'd rather have Bob as my friend. So, I choose to stay with him.
Thanks for all the help!

Answer 1

Bob knows that we are basically the same, so, the first thing he said to me after the break-up was that "You are free to see Jane if you want to, because you are very much like me."

If I were Bob, I'd probably only being saying this to make light of the situation - not as a serious statement. Because of this, I want to rule out the argument of "Well you gave me permission..." before I jump into the meat of my answer. If this was truly right after the breakup, it seems very unlikely that Bob had even had time to process his own emotions, let alone develop enough to be okay with you dating his ex.

That being said, you and Jane have your own history without Bob being present, and it's okay for you to want to date. However, there's not going to be any one answer that guarantees Bob will not be upset with you.

Expect that Bob might need time to adjust to the news, but take steps to help soften the blow:

• Let Bob know you and Jane have been hanging out (if he doesn't already know).

  This will give him an opportunity to deduce this information himself. He might even ask you if you're hanging out in more of a dating way, when he's ready. This step helps 'baby step' Bob into hearing the news of your relationship becoming more serious instead of blindsiding him. This also gives Bob the opportunity to express early distaste of your friendship with Jane, and gives you the opportunity to decide if it's worth escalating any negative opinions Bob is already expressing.

• If/When you tell Bob, focus on how it affects your relationship with him; not expressing how you feel about Jane.

  Hey, so you know that I have been hanging out with Jane a lot these past few weeks/months and I wanted to let you know that our relationship is becoming something more official. I don't want it to strain our relationship, but I didn't want to keep it from you, either.

No matter what your approach and wording, expect that Bob might need some time to fully process his feelings. Say what you need to, be understanding of whatever he wishes to do afterward, and respect that until he expresses otherwise.

• Best case, Bob says it's cool and doesn't care. Awesome. Proceed as usual.

• Most probable case, Bob says 'that sure is something' and wants some time away from you both. Let him have his space. He used to see Jane as 'his' person and now he needs to adjust that mental image to having her back in his life but as 'your' person. Be friendly with Bob but give him space. He'll let you know when he's ready to go back to the norm.

• Worst case, Bob is really upset. Bob doesn't want anything to do with you now, or in the near future. Leave Bob be. If Bob is your business partner, evaluate your relationships' importance in relevance with how your business/friendship is going to be impacted by Bob's extreme reaction and figure out where to go from there (potentially another IPS problem).

Answer 2

How should I approach him if it came to be?

The main point I will add here is don't let Bob find out by bumping into you while your out as a couple.

If you begin to explore a relationship with Jane, be upfront, open, and honest about it with Bob. Remember, girlfriends come and go, good friends are hard to come by.

Carefully consider if its even worth risking it, as you could end up with neither of them as friends.

If you decide to date Jane, do not hide it.

Answer 3

By the sounds of it, your stance is that you're wanting to proceed romantically with Jane, regardless of Bob's stance on the matter. As such, the aim here is simply the best way to break it to Bob. Is that correct?

If so, then I'd do this as early and honestly as possible. The longer you leave it or the more you try and talk around it, the more you risk Bob losing trust in you for going behind his back / keeping a secret from him until the last possible moment. And purely from a business PoV: He needs to trust you.

"Bob, I respect our friendship so want you to keep you in the loop. I've been hanging with Jane and we're considering dating. I appreciate this isn't the easiest thing to hear, but wanted to let you know so we can talk things through and make this as workable as possible for everyone"

Listen to his response, see if you can do anything for him. Then, as Jess K said, give him space.

Ultimately though, there's no approach that will save you if Bob loses it. If you don't intend to stop things with Jane for the sake of Bob... then be 100% prepared for that friendship (and business) to possibly go up in smoke.