Shortcuts: “I Lost My Virginity to My Sister’s Ex”

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.

I slept with my sister’s ex-boyfriend and it was great, but now it’s a little awkward and he still wants to remain friends, and, well, when I slept with him, it was my first time. Should I tell him it was my first time or not? I feel that, if I do, he might shut me out while, if I don’t, I will be withholding something from him that he has the right to know. — No Longer a Virgin

He doesn’t have “a right” to know that you were a virgin any more than anyone else would. It’s none of his business. Furthermore, you slept with your sister’s ex-boyfriend! Be grateful that, given the potential drama and complication that could create, your first time was so “great.” Leave it on a high note and MOA.

My ex and I split up in October after I found out that he was cheating and living a double life. He had a fiancée during our whole relationship. Shortly after we broke up, I found out that I’m pregnant. He’s well aware of this, but he refuses to take any part in the baby’s life. Now, months later, I’ve grown more and more attached to a good friend of mine. My question is: How do I go about telling him I’m pregnant by my ex? I will not, by any means, be one of those girls who tries to play it off like it’s his. That’s not fair. I just want to know how to tell him that I am pregnant. I don’t want an actual relationship right now, but I’m afraid that, if I tell him, he’ll back off and run the other direction. I want to be honest with him, but I don’t want lose him because of it. — Alone & Pregnant

You know how upset you were when you found out your ex-boyfriend had been lying to you/withholding important information? Well, now you’re doing the exact same thing to this new guy if you are pursuing some sort of relationship with him (and whether you say want a relationship now or not, if you care about him and you’re sleeping with him, you’re in a relationship). He deserves to know you’re pregnant, and you should have told him before you crossed the line from friendship to something more. You purposely have kept pregnancy a secret because you have been afraid of losing him, which is exactly the reason your ex never told you he had a fiancée. Yes, this guy may very well “back off and run the other direction,” especially since you haven’t been honest with him from the start, but doing the right thing isn’t always easy and doesn’t always yield you the result you want. Don’t be like your ex. Do the right thing, be honest. He’s going to find out eventually . . .

I fell in love with my boyfriend in 2011. We both love each other, but our families have never accepted us as a couple. Since they never wanted to see us together, the little time we were able to have with each other was time spent making love. Now, four years later, we already have two kids and I am pregnant with his third child. He doesn’t financially support the kids or me, and he doesn’t want me to find a job even though he only earns $780 per month. When I talk to him about getting a job, he always tells me about other men. Am I making a mistake believing that things will be ok? — Pregnant with Number Three and No Money, No Job

There’s so much WTF here, I don’t even know where to start. Have you never heard of birth control? And how in the world are you feeding two children on $780 a month? Why are you letting your boyfriend stop you from getting a job? What does it even mean that your boyfriend “tells you about other men” any time you talk about getting a job? Like, really, what the fuck does that mean? And, yes, you’re making a mistake “believing that things will be ok.” How would they be ok? They’re not ok NOW. How will having a third child to care for and feed make things any more ok? Maybe give #3 up for adoption and get a job already. Also: birth control!!!!


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


  1. I believe LW3 qualifies for food stamps. She should look into that if she hasn’t already.

    1. Avatar photo muchachaenlaventana says:

      I am sure they take advantage of any and all public assistance there is available, there is no way they couldn’t living on $780 with four people to feed.

      1. See, that’s where i’m confused. She says she doesn’t support her nor the kids. And then she says he makes $780 a month. So, if he doesn’t support them, how much he makes is irrelevant.

      2. RedroverRedrover says:

        Yeah, was that a typo on her part? Or is she living with her parents and they’re the ones supporting her and the kids? Or maybe she’s getting welfare and supporting the kids and herself on that. In any case, if he’s not supporting the kids, she should make him. He’s clearly acknowledged they’re his. He needs to take some responsibility.
        Or does “he’s telling me about other men” mean that he accuses her of having kids with the other men? No idea.

  2. TheRascal says:

    LW 2: “My question is: How do I go about telling him I’m pregnant by my ex?”
    Answer: “Hey, I’m pregnant. It’s not yours, but I thought you should know.”
    LW3: ” Since they never wanted to see us together, the little time we were able to have with each other was time spent making love.”
    What in the hell?

  3. WWS, LW1 & LW2…

    LW3 – Whaaaa???? If your boyfriend doesn’t financially support you OR your (and HIS) kids…and you have no job…who IS actually supporting any of you? Why would you ever think this is ok? He is not a supportive partner and he is a deadbeat dad from what you say here. Do you even live together given the Romeo/Juliet nature of your relationship? I am with Wendy – give baby 3 up for adoption, get out of this relationship, sue him for child support, and get yourself back on your feet. You have two kids who are depending on you and you need to focus on THEM, not this dickhead.

  4. Oh LW 3, I have SO MANY QUESTIONS!!!
    So, you already have two children and a third is on its way and you still spend all of your time with your boyfriend “making love”?!?!
    If your boyfriend doesn’t financially support you, who does? Where do you live? How do you take care of your babies?
    As Wendy said…. the other men part…. what the fuck? Seriously. What the fuck?
    I feel really bad for your children. I really do. They deserve better.

    1. Avatar photo Raccoon eyes says:

      ktfran, Im so confused too. I said it below, but I must add that all I can think about is the creepier possibilities (wait, are there non-creepy possibilities about bringing up other men in the context of her getting a job???) about the other men comments… Does he want her to join the oldest profession? Does he? Is he telling her to MOA, maybe? I dont know. I AM DUMBFOUNDED

      1. Does he want HER to see other men so he doesn’t have to pay for anything? Is HE seeing other men (if so… good for you??)? Is he saying “but there are MEN at these jobs and I don’t want them LOOKING at you!” to keep her home?? None of these are even good reasons to not pay child support.

  5. Avatar photo Raccoon eyes says:

    Umm, THese make my head hurt, mostly because I just facepalmed so hard…
    LW1: there is ABSOLUTELY NO RIGHT of anyone to anyone else’s sexual history, other than a heads up regarding STDs. That is ALL. In the future, maybe stay away from your sister’s exes too, mmmk?
    LW2: While you dont want to be one of those girls, you are one of THOSE girls. If this new guy runs in the other direction, then there is your answer: not the guy for you. Also- BIRTH CONTROL and maybe thinking about adoption in your present situation. (I know you learned after you found out about the pregnancy about his “double life,” but condoms, etc are always a good idea.)
    LW3: Umm, yeah, there is so much going on in your 7 sentences that Im just going to say: get a job, get some birth control, get rid of this guy, get some legal advice and get child support, and WHAT_THE_MOTHER-LIVING-HELL does it mean “he always tells me about other men” when you (logically) say speak of jobs?

  6. Avatar photo Addie Pray says:

    I feel all three letters are confused about “rights.”
    LW1 – No, your sexual history, or lack there of, is no one’s “right” to know.
    LW2 – Yes, this guy you’re seeing has a right to know you’re pregnant with someone else’s child.
    LW3 – Those poor 3 kiddos. It may be better if neither parent had rights.

    1. To quote John Prine, their rights are all wrong.

      1. Avatar photo Addie Pray says:

        Spppp, so, BGM’s head got a little big when you wrote him that poem yesterday. And some people I know got so jealous. So I was wondering if you could write a poem for someone else (me maybe?) right here right now, and then, Wendy, um, I was wondering if you could delete this request, and then BGM will be so jealous. Mwahahaha. But quick, guys, before he reads this. Quick. Quicker!

      2. Two things: what kind of dog is Moose again (need details to create a living portrait of you), and would you mind if I rhymed “preggo” with Chicago?

      3. Avatar photo Addie Pray says:

        He’s a Havanese, and not at all! 😉

      4. Well, I had writed this here poem before I saw the response, so havanese is not in there, but here ya go:
        Bikram yoga keeps her bendy
        On many shoes, her dinero spends she
        Her puppy Moose seems very friendly
        Dusky Latina, esta muy caliente
        Powered by a brekky burrito
        Vegan, cuz she don’t eat meat, yo
        A lawyer, but she seems too sweet though
        Stalked by weirdos, but incognito
        On Dear Wendy while she’s billing
        Hope that vegan thing was filling
        She’s eating for two, she’s slightly preggo
        She might be the windiest thing in Chicago.
        She talks about her poop a lot
        Are you that brave? I should think not.

      5. Avatar photo Addie Pray says:

        That’s the sweetest thing any has ever written me. (Wendy, quick, delete that part where I made Diablo write this!

      6. Avatar photo Addie Pray says:

        Oh BGM is gonna be jealous!

      7. Avatar photo muchachaenlaventana says:

        This comment just spurred me to listen to one of my favorite ditty’s “In spite of ourselves” and send it to my baby as its one of our special songs 🙂

      8. Avatar photo muchachaenlaventana says:

        and also I just vommed reading this comment back, sorry guys!

      9. Avatar photo Addie Pray says:

        Oh oh I had a song with my baby daddy (gross, but that’s what he is! ha – whoa, i have a baby daddy) – and it was “Everything Is Awesome” from the Lego Movie. That should have been a red flag. Hahaha.

      10. Yeah, i love Prine. M and I just saw him last year. Very funny and engaging. PS – the motto of our marriage is “Despite Everything.” She actually had this engraved on a lighter for me once.

      11. Avatar photo muchachaenlaventana says:

        I could see getting couples tats instead of wedding rings with something like that. To me, its a lovely and comforting sentiment and really gets at the heart of what love and long term relationships can look like.

  7. We all seem pretty confused about LW 3 as far as how the kids are being fed and the job situation but I have a theory based on a terrible relationship that my best friend was in for several years. They had 4 kids between the two of them and he was the only one who was “allowed” to have a job, yet he constantly quit every job and was content to live on public assistance. Every time she brought up the idea of her getting a job, he would say no because he was certain that a job would lead to her meeting other men and either cheating on him or leaving him. I know, what a controlling douche. Finally, she did leave him and start a successful career. It sounds like maybe this is a similar situation. If so, that’s probably why her family was not supportive of the relationship from the beginning. Others tend to see red flags you overlook.

    1. I was thinking the same thing too. Sometimes when you are in the middle of something like that, it’s hard to come to that “what was I thinking” moment. Good for your friend.

  8. LW1 – WWS. Nothing good can come of making this situation into a big deal.

    LW2 – He has a right to know you’re pregnant with someone else’s baby and that youre not interested in a serious relationship. I’ve never understood how people can treat new boyfriends/partners/whatever with the same form of disrespect that they’ve experienced firsthand by someone else. (In this case, lying and withholding major information.) He’ll figure it out eventually…

    LW3 – I’m equal parts confused and saddened.

  9. Wonderland says:

    LW3 – I wonder if the “other men” thing is less of a jealousy thing, but more of a dick measuring “All my brothers, cousins, etc support their families – a “real man” makes it so his wife/gf doesn’t have to work”. More of a man-as-provider thing than concern she’d cheat. Just a thought. Still not awesome but slightly less awful (like 0.02% less awful)

  10. LW3, things are not okay, never were okay, and are unlikely to become okay.

    My guess is that you were young and/or inexperienced before getting together with your boyfriend, and your desire to be “in a relationship” is so great that you allow yourself to be treated this way. You can do better for yourself. You can do better for your babies.

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