The 4 Most Memorable Sexts I’ve Caught Boyfriends Sending
My theory on sexting is this: whether you’re the best boyfriend or the worst boyfriend, you’re going to engage in technological infidelity at some point in a long-term relationship. If it’s a mild innuendo-laced conversation with an ex on the day of their would-be six-year anniversary, or an actual photo of actual genitalia saying “LET’S TALK ABOUT THIS D***,” most of us have caught our significant other with their password down. Here are the four most absurd, shocking, amusing, hurtful and downright hilarious sexts I have caught various boyfriends sending to other women over the years:

1. The sext: “I had a dream last night about fucking your big beautiful tits.”

The boyfriend: A young South African Coast Guard guy who pledged his undying love to me within days of meeting (so what I’m saying is, there were no red flags from the get).
The situation: My brother’s wedding. He was a perfect date. I later got drunk and hacked his phone (who uses their birth year for a password? It was 1986, by the way #teamcougar). What I found was a text to a Kristina explaining his aforementioned sex dream he’d had about her while sleeping next to me in a luxurious hotel bed. Maybe it would have been forgivable had it not been sent DURING THE CEREMONY. What a romantic. But it didn’t matter. I flipped out like a Grey Goose-soaked bridesmaid maniac and he dumped me on the spot for invading his privacy. Like, he flew home to Boston on a plane without me that morning. I got dumped for HIS sexting. Alanis would have a field day with that degree of irony.

2. The ‘sext’: “m4m can host”

The boyfriend: A rowdy drunken Irish carpenter I dated for four years who was, initially, outwardly homophobic.
The situation: I was out of town one week. When I returned to our house, I found on our shared computer an advert he’d posted on craigslist seeking blowjobs, and not just any beejers – ones from guys. Funny enough, I found this one to be quite forgivable, only because I’m open-minded in a sexual-experimentation way, and we had a candid conversation about fluid sexuality, bisexuality, and the like after I called him out on it. It was indeed absolutely freaking shocking at the time, and yes, I berated him from the infidelity angle, which was deserved since this was more than a sext. He was actively trying to make this happen. He claims he never cashed in on the head, but I sincerely doubt he went looking for a drunk down-low blow job and couldn’t find one. I don’t see him anymore, but I hope he has found the woman – or man – of his deepest, darkest dreams.

3. The ‘sext’: “I want you back.”

The boyfriend: At the time, a newer boyfriend, but a guy I had known a long time. He was sort of a dope-head, Eminem-looking suburban kid from my hometown with a huge….ego.
The situation: This was the most crushing of sexts, because it was not even a sext at all. This pure kind of emotional infidelity is the most painful and unforgivable. You can imagine that a penis might stray, but not a heart. It was about wanting to replace me with his previous girlfriend. He had left her for me when we’d first hooked up. But I suppose when the initial fireworks between us wore off, he wanted to get back to his easy, original girl-from-before, not some batshit-crazy older chick he’d crushed on back in 1997. This was years ago and I know they’re still together. These are the texts you want to watch out for, ladies. Dick pics are explainable (“I was horny”). Feelings are indefensible (“I love someone else”).

4. The sext: “Remember these?”

The boyfriend: The current babe in my life. Has knuckle tattoos, works on the railroad, and is sickeningly brilliant at crossword puzzles.
The situation: Last year, I caught my boyfriend sending his ex a photo of himself in his Batman underwear. I found the photo before I saw the text and he swore up and down it was for “his own photo library”. Which I found even creepier, to be honest. You take pictures of yourself in only Batman underpants? Watch out, Gotham, we’ve got a real hero on our hands now! When he fessed up, he explained he was feeling insecure about our relationship because I was still very (non-sexually) friendly with one of my exes. He said he sent the text “out of nostalgia” because she’d bought him the undies and they both loved superheroes and comics. This is one that you have to let slide, because it’s fairly harmless. The story lined up. Inappropriate? Hell yes. Unforgivable? Nah.

Why? Because we live in a modern world where the past follows us around like a stalker. Exes stare us down on social media daily, smart phone texts almost send themselves like latent inner thoughts diving onto a screen, sometimes while you’re driving or even SLEEPING (I’ve sent a full-on SLEEP TEXT about Hooters and getting beers at 4am. WTF?).

So let’s say your lover catches you mid-sext, or vice versa. The thing is, if everything else in your relationship is pretty awesome, and the offense is pretty minor, you have to know he or she cannot autocorrect their mistakes. Just look inside your heart and download your inner iForgiveU app (note: There is a usage limit on this this app, because your BF should only require it sparingly). Think long and hard about it. I’m sure that at least once, that one time when Dave didn’t call back the night he was in Vegas and you were at a work happy hour, you MAY have shot a pretty slutty text to your college ex that you wouldn’t want Dave to view in the sobering light of day.

So let’s not chastise too hard. We love our phones. We love our lovers. So loosen the reigns and let it be. The good ones won’t take it too far. Give one or two passes if you’re happy otherwise. Unless he’s sending snaps of himself wearing superhero underwear, in which case, make fun of him relentlessly. And possibly buy a Catwoman suit so he takes pictures of you. Thought Catalog Logo Mark

More From Thought Catalog