“I Cheated With His Best Friend”

It’s time again for Shortcuts. For every question, I’ll give my advice in just a few sentences because sometimes the answer to a person’s question is so obvious and the need to hear it so great that being as clear and frank as possible is simply the best way to go.

So this guy and I are not officially together, but I “really really like” him. I’m also really insecure. And last night I got really drunk and accidentally had sex with his best friend. I barely remember it, but, yeah, it happened. I’m a terrible person. I feel disgusting. I hate cheaters and now look at me. What should I do?! — Now a Cheater

If you weren’t together with the guy you “really, really like,” then you couldn’t have cheated on him. You did probably blow your shot at “officially” being with him, but something tells me that chance was pretty small already or it would have already happened. Still, if you want to know where you stand with him, just ask him. If you don’t like his answer, you can always see where you stand with the bestie. Is he cute?

My ex and I have been broken up for five years now, but we’ve continued having sex off and on. During one of our off times he got into a relationship with this girl from his job. We reconnected like we always did, but this time he was cheating on someone. I moved to a different state hoping to give his relationship a chance now that his girlfriend is pregnant. I recently went back to my hometown and we somehow got reconnected like we always do, and he cheated on his pregnant girlfriend with me (on the day of their baby shower, which I had no clue about). He texts me every day telling me he can’t live without me and he doesn’t want to lose me and that I just need to have patience. I don’t want to ruin his family, but part of me feels he knows he made a mistake and he’s trying to fix it. Should I leave this situation alone for good even though I feel he’s the only guy made for me? — He’s Made for ME

Yes. The guy’s feeding you, and who knows how many other unsuspecting women, a bunch of BS. Be glad YOU aren’t the one who’s having his baby and will have to be tied to the loser indefinitely.

My guy and I have been together for almost four years. He became very depressed at the beginning of last year. He would tell me he didn’t love me, and he didn’t know if he wanted to be with me or not. He stopped talking to me. We only had sex when he wanted it. I tried talking with him, but he wouldn’t talk. So, I did a horrible thing and started dating another man. He found out and moved out. We never stopped seeing each other, but, in the midst of all this, he impregnated another woman. We decided to work things out, and now I want to know, since we’re back together, if I should help him financially with the child? — Reunited and It Feels So Good

Hell. No. Also: use birth control. Lots of it.


Follow along on Facebook, Twitter, and Instagram.

If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.


  1. What is with all the shady sex and “accidental” pregnancies.
    LW1- you didn’t cheat, he may not have been that into you anyways but 100% you guys aren’t getting together now. Don’t feel bad though, there will be other guys you’re interested in and in the meantime work on your self confidence – have you tried taking classes in something you’re interested in (like dancing, drawing, cooking etc) or joining a league ( my city has an athletic organization and has leagues all year for all sports – you can come in with a team already or join one)

    LW2- this is the man you want? “We somehow reconnected” no you reconnected because you’re actively pursuing someone who is a ) not interested in you and b) cheating on his pregnant girlfriend. Don’t end up as the other pregnant girlfriend he’s cheating on.
    LW3- You want to help him with his child support for a child that’s not yours? Good lord, you’re not even an official girlfriend let alone step parent. Let him sort out his own mess and don’t become like the idiot women who pro created with these guys!

    1. Avatar photo muchachaenlaventana says:

      I know!! Or like the “seeing each other” aka banging (apparently without protection).

  2. TheRascal says:

    “accidentally had sex”
    “somehow got reconnected”
    These two phrases bother me. Please, ladies. Take some responsibility — one cannot “accidentally” have sex. One doesn’t simply “somehow” reconnect with someone. Both of these take deliberate action.
    LW3: Leave this man.

    1. But what they have is extra special, dont you know? Who cares that theyve been broken up for 5 YEARS

      Seriously, take some damn responsibility. And use some damn BC. Contrary to what it might seem from some letters on here it´s not actually hard to not get pregnant.

      LW3 goes for you too. I´d also like to know what part of the reunion feels so good.

      I always look forward to shortcuts, but then they just make angry haha

    2. There does seem to be an epidemic of lack of agency around here…

    3. Lily in NYC says:

      This! Using the passive voice doesn’t make you less culpable for your mistakes. #2, sleeping with your ex on the day of his baby shower is all kinds of low.

      1. Avatar photo LadyinPurpleNotRed says:

        To be fair, she says she didn’t know it was his baby shower…granted that doesn’t excuse the fact that she was helping someone cheat on his pregnant girlfriend, but still. There is enough shitty things going on that we don’t need to make stuff up.

      2. Lily in NYC says:

        A reading comprehension fail is not the same as “making something up”. Ouch.

      3. Avatar photo LadyinPurpleNotRed says:

        I apologize. It could have been either one.

    4. Amen. LWs, accept your part in your situations.

  3. No relationship with this much accidental drama (accidental sex, accidental reconnection, accidental cheating, accidental pregnancy) will end well – or even start well, for that matter.

  4. monkey's mommy says:

    LW 1: you answered your own question in the first sentence-you are not officially together! You did nothing wrong!

    LW 2: you are an idiot. And a homewrecker. And a few other choice words I’d like to call you. He is telling you what you want to hear so he can keep banging you when you come around. Leave him alone!

    LW 3: what are you doing???? You were unhappy enough to cheat. He said he doesnt love you because he was “depressed”. He knocked someone else up. And you want to get back together and pay child support?? Run!!!!!!!!

  5. Can anyone hear then sound of my head slamming onto my desk? Ugh…….

  6. LW1: There’s no such thing as ‘accidental sex’. You chose to sleep with the guy. Own it and stop making excuses. Being drunk isn’t an excuse for anything, because you chose to do that too.

    LW2: You talk about all this reconnecting like it’s something you had no part in, that he’s doing it on his own. Again: choices. He ‘cheated with you’? You had nothing to do with that? You could have said no. You chose to say yes. You were every bit as guilty in the cheating as he was.
    Either tell him that you’re done with the reconnecting until and unless he’s not in a relationship with anyone – and then cut off all contact – or just forget him and MOA.

  7. Sue Jones says:

    Facepalm Friday! Birth control birth control birth control!

  8. Oh man, I really hate when I accidentally have sex with someone. I mean, I’m just standing there minding my own business and my clothes just fall right off and then I trip and fall on top of them! It’s terrible.
    Anyway… LW1 – You didn’t “accidentally” have sex with him. You made that decision. Yes, your decision making skills were probably impaired because you were intoxicated, but that doesn’t forgive you of your own damn responsibility. You weren’t with the guy, so you didn’t cheat. And obviously you don’t “really really like” him that much if you slept with his best friend. If you want to see where you stand, ask him. Or ask the friend. Whatever.
    LW2: Stop that right now. You don’t just somehow “reconnect” with people. You actively do it. So knock it off. You know he’s with someone else and you know they’re pregnant, so you should keep your vagina to yourself. He’s playing you (and the pregnant girl and who knows how many others) so delete his number, block him on facebook, twitter, instagram, whatever and move on with your life. Let go of this mess.
    LW3: Depression sucks, but it isn’t an excuse to be an ass and tell your SO of 4 years that you don’t love them. And then he knocked up some other girl? Nuh uh, you need to move on. And certainly don’t help him financially support this kid. It’s not your responsibility.
    And for all three of you – please use birth control. Multiple forms.

  9. Avatar photo Addie Pray says:

    WWS. Also, TGIF, baby!!!

  10. Is this really how people think? That sex just “accidentally” happens? That you “somehow” reconnect with someone? Please, people. Are you drones? Do you have no mind? Please admit that you contributed to each of these situations. If this is the state of the world, I need to step up my plans for that sheep farm in New Zealand.

    1. Can I join you? Maybe I’ll start a vineyard.

      1. Absolutely! I’ll have to throw in some chickens. I love chickens. We’ll be set.

      2. Awesome. Self sustainable commune. I like it.

  11. All you haters, you can TOO accidentally have sex with someone! That’s what happened to me! Our first time, in M’s OWN WORDS, she got me drunk, tripped me and then beat me to the floor! She ensnared me with her sexy sex and I had NO CHOICE! All these years I’ve been a VICTIM of her calculating PLOT! So next time maybe THINK before you JUDGE! I like exclamation points! AND ALL CAPS!!!

    1. Hilarious. Wait. No. HILARIOUS!!!!!!!!!

      1. OH. EM. GEE. Tripped you and beat you to the floor? I am gonna be laughing at this all weekend!

    2. That damn sexy sex. We are all vulnerable.

  12. “keep your vagina to yourself” (by honeybeenicki), best advice ever! (let’s call it KVY)

  13. Bittergaymark says:

    “Somehow” I have nothing to say to all these clueless fools. WHOOPS! WTF ?! Sorry, I only “accidentally” said that shit. (Fucking losers!). Omigod. Yikes! It’s happening again! I don’t understand. (Never breed! Go waste your lives as a muthafucking nun–all of you!!) Oh horrors! Help! I’d best log off before I “just happen to post this meanness…

    1. Bittergaymark says:

      God grief! That wasn’t supposed to post!?! My iphone must have — I dunno — I guess — “reconnected…”

      1. It’s ok, it’s obviously not your fault that you somehow accidentally reconnected with it.

      2. Avatar photo Moneypenny says:

        But do you “really really like” it? That’s the burning question.

  14. Skyblossom says:

    LW2, you’ve been broken up for five years and you keep seeing him. How long are you going to put your life on hold waiting for him to realize that you are the love of his life and that he should be with you? Isn’t five years enough, isn’t his girlfriend being pregnant enough, isn’t the fact that he cheats enough to make you give up and find a worthwhile boyfriend. One that loves you and is loyal to you and who has enough character that he doesn’t cheat. How many years are you willing to be patient, while he has his girlfriend and he has you and however many other women he can string along. Run away from this situation, don’t look back and be glad that you are the one that got away and not the one who is pregnant. How many lost years are you willing to have? Do you want to give him a decade of your life? He will take as many years as you are willing to give.

  15. LW2, each time you somehow get reconnected, does the wind magically blow a piece of paper into your hand with his new phone number on it? Does a glass bottle arrive at your feet while you’re walking on the beach that holds a love note from him? No? THEN YOU ARE NOT “somehow getting reconnected”. The universe is not throwing you together. You are DECIDING to pick your phone up and reply to that text/phone call/email, DECIDING to see how he is and what he is up to next weekend. You’ve been making that choice for 5 years now. You’ve continued to make that choice even though he has a baby on the way. That’s pretty awful of you, but since you aren’t taking any responsibility for your role in being the other woman, you wouldn’t know that. Stop. Talking. To. Him.

    1. What? Life doesn’t just happen to you?? You have personal responsibility for your own decisions???

  16. LW1, I thank you for offering the perfect set up for a West Wing quote (tailored to your situation):
    -Last night I accidentally slept with my boyfriend’s best friend.
    -You accidentally slept with your boyfriend’s best friend?
    -Well technically we’re not officially together.
    -I don’t understand. Did you trip over something?

    As for actual advice… yeah, I’ve got nothing except all of you please use birth control.

Leave a Reply

Your email address will not be published. Required fields are marked *