Worst-Case Scenario
I’m a 25-year-old guy, and I have been involved with an older woman, she’s 44 years old, lately. It started a few months ago when I was on Tinder trying to find someone to hook up with. I saw this very attractive older woman and decided to swipe right because you know, it’s every 20-something-year-old’s dream to hook up with a MILF.
A few days go by and I get a notification that I have a new match. Wahoo! I open up the app and lo and behold it’s the fine cougar I was hoping for. We start chatting and flirting, and it’s going really well. Out of nowhere, she messages me and says, “I’m not sure how this app works, do we just meet to get it on or do we go on a date first?”
I was drinking coffee at the time and promptly shot it out both nostrils. My chance had come. I replied back that people generally just meet up to go to the Bone Zone together but I’m easy either way. She replies, “Well good, because I hate formalities.” I nearly pooped my pants in excitement. She sends me her address and tells me she’s free on Friday and to bring a bottle of red.
The rest of that whole week was a complete blur of anxiety. I could not screw this up. So Friday comes, I show up with a bottle, and she looks really, really hot. Even better in person. We talk about music and traveling and all that, not many personal details (which would come back to haunt me) just sort of arts and culture talk.
A few glasses later and we’re full-blown going at it. I left a little while later feeling like I’m the king of the entire universe and go to sleep. The next day, she texts me saying how she had a great time, and it made her feel young again and all of that. She says she’s off every Friday and Saturday and that next week we should do the same.
This has been going on for roughly three months now. We meet up once or twice a week and then go on our merry way until one of us gets in the mood again. Sweet deal right? Well, I just found out how wrong I was. I messaged her yesterday saying that I had today off of work and asked if she wanted to meet up. She said her son was taking her out to lunch, and that I could come over at 3 pm.
She had mentioned she had a son before but didn’t go any further and I didn’t really care to ask. So 3 pm comes and I’m almost at her house when she messages me that she’s running late. No problem. I park on the road and sort of just wait in my car because her car wasn’t in the driveway yet. I’m sitting there listening to the radio when an oddly familiar SUV pulls into the drive.
I sort of looked at it funny, and then I immediately realized where I knew it from. My co-worker jumps out of the front seat, goes around to her side of the vehicle, gives her a kiss on the cheek and a hug, and then jumps back in the car. My jaw was on the ground. He reversed out of the driveway, and stupid me is sitting like a deer in the headlights in plain sight.
He turns around and is literally 10 feet in front of my car and staring directly at me. My face goes bright red and I feel like I’m going to vomit. Me and this guy work together every single day and I consider him a friend of mine. I even trained him when he started at my company. And the kicker is, I’ve been telling him (in detail) about this older lady and he’s been giving me immense kudos about it saying that it’s “his dream.”
He pulls up beside me and looks very confused, asks me what I’m doing, and says how funny it was we ran into each other. I panic completely and stumble over my words and pretend like I’m on the wrong street and trying to find my cousin’s house. He looked skeptical but sort of shrugged it off. The whole time, his mother is standing there watching us through the curtains.
He directs me where to go and I pull off and then circle back once he’s gone. Needless to say, I went inside and told her what was up, and we both sort of sat there in silence before I left. No boom boom that day. I am now panicking because I think there’s no way he’s not going to know, and he’s going to realize all these wild escapades with this she-devil night mistress I’ve been telling him about is actually his mom.
Later, she texted me and says that we should tell him and come clean because it’s the right thing to do. She was adamant about telling him, even after I informed her about the explicit details I’ve been sharing since we started doing this. What is wrong with this woman? She keeps insisting that “he’s a grown-up and he should realize that his mother is a person too with desires like any other person.”
She said regardless of what I say, she was going to tell him the next day because she can’t “live with the guilt and deceit.” So eventually, the cat got out of the bag, and she came clean about it all. My co-worker called me saying it was super weird and his head is spinning but he’s not mad because he knows we had no idea. He asked if it was her I’d been talking about the whole time and I said yes.
He paused. Then he asked, “…even all that crazy stuff?” RIP BRO. Needless to say, I laughed and changed the subject, you’ve been through enough my child. He also said he’s going to look for a new job and already gave his two weeks’ notice because it’ll be weird working together. He genuinely just seemed bummed. He also said he put in a transfer so we won’t be working in the same building until he’s gone.
Jeez. I’m going to see his mom later and tell her we can’t do this anymore. She caused him to lose a job and a friend and gave him a reason to go to therapy over something we could’ve likely played off.