Background image: The Bold Italic Background image: The Bold Italic
Social Icons

Should I Tell My Friend I Slept with Her Boyfriend? — The Bold Italic — San Francisco

3 min read
The Bold Italic

When it comes to good advice, Jessica Lanyadoo has it in spades. The Mission’s resident psychic/astrologer/badass gets booked months in advance by San Franciscans seeking help with everything from figuring out their love lives to communicating with their pets. So we asked Jessica if she’d come on board to do a weekly advice column for The Bold Italic. If you have a burning question for Truth Talk with Jessica Lanyadoo, email her at truthtalkwithjessica@gmail.com, and check back on Wednesdays to see if she has an answer for you.

Hi Jessica,

A while ago, I slept with a coworker. I’d had a crush on him for a few months and when I was finally single, I decided to sleep with him. I was drunk. When we got back to my place he let me know we had to keep it a secret. Sounded perfect to me. The thing is, he was dating someone we both worked with. She was younger than me and really looked up to me. I ended up having an affair with him for a few months until I realized how crazy he was. I regret it immensely and I never told her. I feel bad because she texts me to hang out and frequently visits my Facebook page. I know what I did was wrong, and I hate that I did it. They are still dating to this day (it’s been over a year since he and I ended it). Should I tell her? –OOPS

One of the great joys of being newly single can be hooking up with that cutey you were eyeing when your relationship took a nosedive. I would say huzzah for you, but of course it’s not that simple here. It’s like you gave yourself the joys of a fun and dirty rebound, but you packed it full of negative consequences that were guaranteed to haunt you. Regardless of what you do here, I encourage you to make sure that the next time you give yourself a gift, it’s one you can actually enjoy.

I’m not sure it matters at this point, but I’m curious if you knew he was dating your co-worker when you first slept with him? If you had drunkenly hooked up with this guy and didn’t know that he was dating a friend of yours, that’d be innocent enough. If you did it just the one sloppy time knowing that they were an item you might even get a pass. But you didn’t just bone him once, when you were half in the bag. You must have known that you were having a secret affair while it was actually happening for all those months. You’ve clearheadedly been lying to your young friend for more than a year, so why the need to tell her now, OOPS?

You say that you realized how crazy he was somewhere at the end of your affair. I hope that you aren’t pissed at him and wanting to get some sort of payback. If that’s the case, even a teeny tiny little bit, you need to be careful. You aren’t an innocent party here and it’s not fair to drag his GF into this mess if your true motivation for coming clean is for him to have to suffer the consequences.

But ultimately it sounds like you feel appropriately awful, OOPS and that you’re trying to make things right. I’m afraid my advice is the same, though. Don’t do anything! It’s not fair to sleep with a girl’s boyfriend for a few months and then let more than a year pass just to spring this stuff on her. What you’ll be telling her is that you’re not really her friend because you’ve let her think her boyfriend was her own when you knew he wasn’t for all this time, and that her boyfriend sucks. How’s she supposed to feel about all that? I would imagine it would make her feel beyond terrible. It might abate you of your guilt but I’m afraid that you missed your chance to tell the truth in a way that would actually help the situation and be fair to her. I encourage you to deal with your guilt but please oh please don’t just dump your dreadful feelings in her lap. Your guilty position is only helpful if you can allow it to humbly guide you to make better decisions in the future. Life isn’t about being perfect, so learn from your mistakes and move on, OOPS.

xo

Go to www.lovelanyadoo.com to read Jessica’s free weekly astrology column or to schedule a reading.

Tagged in:

Advice

Last Update: September 06, 2022

Author

The Bold Italic 2415 Articles

Subscribe to our Newsletter

Subscribe to our email newsletter and unlock access to members-only content and exclusive updates.