We’ve all slept with someone we shouldn’t have. Whether it was a one-time thing or something ongoing, we wish it never happened. We may laugh about it now, but at the time, it wasn’t so funny. Sure, we’d love to live by the “no regrets” motto, but let’s be honest — there are definitely some intimate encounters you could have done without.
The first time you did it after you got out of a long-term relationship. It’s never easy to be physical with someone else when you’re used to sleeping with the same person for five years. He probably didn’t do that thing your ex used to do that you loved, and likely you had your first post-breakup intimate encounter way sooner than you were ready for. For some reason, this kind of experience usually ends in tears.
When you slept with your co-worker. Maybe it was the office Christmas party after a few too many drinks or on that business trip that gave you and the attractive guy from finance a lot of alone time. You may have enjoyed it in the moment, but you definitely regretted it when you got back to the office. How are you ever supposed to concentrate when he’s walking past your desk and you can’t stop picturing him naked?
When you slept with your best friend. Well, that didn’t go according to plan. There comes a time in many female-male friendships when you sleep together. Maybe you were drunk, maybe you both hadn’t done it in a while, or maybe it just seemed like a good idea since you spend so much time together. Whether it ruined your friendship or just made things plain awkward, you probably wish you didn’t give the whole friends with benefits thing a try.
The time you slept with a married man. You probably had no idea he was married, but once you find out, you couldn’t help but feel sick. You felt guilty for months, even if he told you he was single. While not your fault, you definitely wish you can remove that one from your kill count.
Your first experience with an added person. It’s never really what you hoped it would be. It may sound exciting, but in reality, it’s more uncomfortable than anything. You probably didn’t know who to pay attention to, what was coming next, or how to satisfy two people while also making sure you got satisfy yourself. In the end, you likely didn’t even come. Looking back, at least you can say you tried.
When you went back and slept with your ex-boyfriend. You broke up for a reason, but that reason likely wasn’t anything to do with the intimacy. It happens. Whatever the reason, we’ve all ignored our friends’ advice and went back for one more rendezvous with the man who broke our heart. Whether you hate yourself for giving in to his nonsense or you hate the fact that now you can’t stop thinking about him, you wish you would have listened to your friends when they said you’d regret it.
Drunk intimacy with the random from the bar. Does this ever turn out well? Not only was the sex terrible, but now you’ve got this man beside you who looked much better with your beer goggles. As soon as the awkward small talk started in the morning, you wished you had paid for your own drinks the night before.
Sleeping with the guy who didn’t deserve you. What is it about the loser that makes you want him so bad? Sometimes we can’t help but be fiercely attracted to the guy who messes us around. We’d love to stand up and tell him we deserve better, but it doesn’t always happen that way. We fall for his sweet-talk, get caught up in the moment, and somehow convince ourselves that he’s looking for more than a casual encounter. But when you quickly realize that’s not the case, you hate nothing more than the fact that you let him win.
When you slept with your neighbor. Sure, it’s convenient, and everyone wants to be “girl next door” at some point in their lives — but what happens when it doesn’t go anywhere beyond that night, or when it ends badly? You hate seeing him bringing home other girls, you hate that you run into him all the time and have to make awkward small talk, and you hate that you’ve considered moving out of the place you love just to avoid him.
The time you slept with a man twice your age. We’ve all been attracted to a much older man at some point in our lives. Maybe we were tired of dating men who didn’t have their lives together, so we found it incredibly attractive when we met a man who did. Perhaps it had something to do with the way he was able to take care of you. Or maybe he’s just a silver fox who happened to woo us with his intelligence. But let’s be real — this relationship was doomed before it began. It was never going to work out. Looking back, you shudder. You just can’t help thinking that he was old enough to be your dad.
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