As many have already said, this is going to be complicated, and frankly, probably not going to go well. First things first, talk to Martha directly. See what her feelings are, if she remembers you, how much Jenn knows of her past life. Then, and this is a must, you need to tell Jenn you slept together. My personal point, and I know others will disagree with me, is that you in no way whatsoever need to mention this was an escort/patron relationship. You were not with Jenn when that happened. Jenn does not go over every sexual encounter she's been through with you. I'm sure you have not gone over every sexual encounter you've had with her. Hiring an escort is no different than a one night stand and you have no reason to have to tell her about it. If you feel you want to, then that's one thing. But this does not fall into the category of "wronging" your SO so frankly, it can stay in the dark. Explain that your first lunch was awkward because you didn't know how to bring it up. But to be clear, if you feel that that would be lying, then you need to tell the whole truth. If the roles were reversed and you feel like she absolutely would have to tell you if she'd slept with an escort, then you owe it to her to tell her you did. If there's an inkling in your mind about feeling like leaving that information out would be wrong, then you need to tell her every detail. Because that will always haunt your relationship. Frankly, Martha's potential secret is hers to keep, not yours. She chose to be an escort and that comes with the risk that someday, you'll run into a patron in your everyday. It is your past and you are allowed to divulge every detail about it if you wish. You can talk to her about how you'd like to tell Jenn, but she cannot force you to not tell Jenn. Then, Jenn will do whatever Jenn feels she has to do. You can't control her. You'll need to accept how she reacts. From there, normal relationship stuff. Don't let people in this thread shame you for sleeping with an escort, especially when you were single, you were in a rough place, and you just needed some company. You did nothing wrong. You have no need to explain yourself. Just clear the air between the three of you that you have "known" Martha sexually and let the chips fall there.