Dear Wendy
Dear Wendy

“He Confessed to Sleeping With Someone Else”

I’ve been seeing a new guy recently and we’ve been out four times. We had sex on our second date, a Saturday night. He seems smart, funny, and not creepy, but on our fourth date, he said something weird. He asked if I had had sex (with anyone else) the night before I’d first slept with him. I laughed, made some joke about the question, and said no. Then (and I should have seen this coming), he told me that he had hooked up with someone the same weekend we hooked up, and “wanted to be honest about it so I wouldn’t be hurt,” and also said he was asking to “see how I would respond.”

I’m really bothered by this — not that he had sex with someone while he was getting to know me — but that he overtly tried to ‘test’ me, his sole motive being to catch me off guard and see if I handled it in a way that he liked. I was taken aback and thought aloud a bit about how, as a single person, he is allowed to sleep with/do whatever he wants, and that I was perplexed as to why he had ‘confessed’ this to me, since he hadn’t done anything out-of-line. I told him it’s a little unfair to test me like this, because he trapped me into a conversation and mental image that was awkward and unnecessary, since we are just really getting to know each other. If he had simply asked me how I felt about dating multiple people at once, that would not have been a weird conversation.

He has said previously that he’s wary about girls, having been hurt before, and doesn’t like what he sees as annoying general patterns of girl behavior in relationships. As a feminist, I found this eye-roll inducing, and after this most recent conversation I’m even more annoyed. My question: Is his behavior just quirky but otherwise reasonable, or am I justified to feel this is not a good sign? — Way Too Selective?

Playing a little diddy on a ukulele for a cat is quirky; wearing a real bowling shirt with the name “Frank” on the pocket for a bowling date is quirky; owning a vintage pachinko machine is quirky. Asking someone you’ve gone out with four times if she slept with someone the same weekend she slept with you for the sole purpose of telling her that you did just that is … rude. And … tacky… and kinda creepy. I mean, I’m with you. If he wanted to gauge your reaction about dating multiple people simultaneously or make sure you weren’t more invested in your “relationship” than he was, or whatever, he should have just come out and asked those questions, not a personal question about your sex life. And he sure as shit shouldn’t have “confessed” that he boned some chick the same weekend he slept with you.


Seriously, this guy lacks class, and that fact that he actually told you he’s “wary of girls” because “he’s been hurt before” means he’s a tool, too. You’ve been hurt? Aww, welcome to life, little guy! Sometimes, sucky things happen! You had some bad experiences in dating? How unique! And quirky!

For all the reasons you gave, this is a good guy to MOA from. You are not being “too selective” by demanding a little respect and an ounce of maturity. And you know what you should say to him when you let him know it’s over? This: “Hey, do you ever go out with someone a few times and think it’s going well only to realize the person is sort of a tool and you don’t want to see them anymore?” “No?” “Oh, well, I only ask because, ha ha, that’s exactly what has happened to me! With you! I’m just trying to be honest so you won’t get hurt! Tee-hee!”

*If you have a relationship/dating question I can help answer, send me your letters at wendy@dearwendy.com and be sure to follow me on Twitter.

93 comments… add one
  • Leyahn May 18, 2011, 7:26 am

    He just sounds, eeewwwww.
    4 dates – you have nothing invested – just MOA

    Nota Bena: you may want to consider waiting a little longer than the 2nd date to have sex – then you would have found out he was a creep before exposing yourself to STDs and such with him.

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    • LTC039 May 18, 2011, 9:35 am

      I get where you’re coming from, but it’s not a known fact she’s contracted STD’s…It’s a possibility, but you don’t really know.

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    • spaceboy761 May 18, 2011, 9:54 am

      I agree that a large proportion of DW letters could have been preemptively solved with, “Don’t bang so fast”. It’s definitely a trend. Anyone who says that they could have any clue who somebody is after one date is either lying or deluded.

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      • Desiree May 18, 2011, 11:07 am

        THIS. At least, that’s my opinion. But some people just have a more relaxed view towards sex, and that’s cool too. But if that’s the case, complaining about the collateral damage seems unwise.

    • leilani May 18, 2011, 9:59 am

      I don’t know that this would’ve been solved if they didn’t have sex. The guy would still have had sex with someone else the day before, and I can’t imagine that the way he handled the situation would’ve been any different. Cause whether you think he felt bad or he was being manipulative, that probably still would’ve case and he still would’ve opted to say that stuff.

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      • Amy May 18, 2011, 10:04 am

        Yes – but she wouldn’t have been physically involved with him at that point.

      • leilani May 18, 2011, 10:09 am

        Yeah, but if she’s having sex with people really early on, maybe that’s because it isn’t as big a deal to her as it is to you. To me having sex with someone I’m seeing isn’t that huge of a deal, and if I went out with a guy a few times and we broke it off, I wouldn’t be more upset because I’d slept with him. I imagine if you’re the type of person who likes to wait longer, the fact that you were “physically involved” would be of greater importance.

      • spaceboy761 May 18, 2011, 10:09 am

        Yes, but without rushing into the banging phase of the relationship, the LW wouldn’t have been stuck with the mental image of essentially being two-timed, which is her primary hangup right now. It would be a much smaller issue.

        Sidenote: This is yet another case of a woman writing in asking for permission to breakup with a guy. Nobody has to justify your feelings.

      • leilani May 18, 2011, 10:12 am

        I don’t think feeling two-timed is her primary issue. She says in the letter that she wasn’t bothered that he was having sex with someone else, but that he opted to use it to “test” her and make her uncomfortable.

      • spaceboy761 May 18, 2011, 10:20 am

        After re-reading the letter, I absolutely agree with you, but I also think it’s possible that the LW is really hurt about being two-timed and is just projecting it elsewhere because denial ain’t just a river in Brazil. Either way, we’re splitting hairs because it doesn’t functionally matter whether she’s dumping a scumbag, a moron, or a drama queen. Just ditch him.

      • Blitzen May 19, 2011, 2:12 pm

        denial ain’t just a river in *Egypt*. Just sayin.. =P

      • Hana May 18, 2011, 1:23 pm

        I didn’t see her as feeling two-timed at all. She clearly states that he was allowed allowed to sleep with other people as they were dating and dating multiple people at once is ok. Her problem is that he tried to test her to see if she would respond how he would like. And that is disgusting. That is rude and manipulative.

    • jena May 18, 2011, 11:54 am

      If they hadn’t had sex the second night, he wouldn’t have asked the weird question. She wouldn’t have “known he was a creep” and may have still slept with him down the line — at which point, he STILL would have slept with the girl before her, so the whole “expose yourself to STDs” argument falls FLAT.

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      • Krissy May 19, 2011, 12:04 pm

        I think she should of waited a little longer to get the know the guy. I normally wait after I know someone’s middle name to sleep with them.

    • alletron May 18, 2011, 7:33 pm

      How about not slut-shaming.. that’d be cool, right?

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  • Callifax May 18, 2011, 8:10 am

    No, not justified. Definitely totally weird. Maybe there’s someone out there for him who will enjoy passing his “tests” and not mind being told about his sexual exploits, but I don’t think that person is you. Cut your losses and move along!

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  • Lexington May 18, 2011, 8:14 am

    Yeah, this guy is totally immature. Next!

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  • Jess May 18, 2011, 8:17 am

    hahah please say exactly what wendy said to it would be so funny!! he might even realize what a creep he was too

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    • spaceboy761 May 18, 2011, 10:23 am

      Say it? I would broadcast it on YouTube.

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      • ReginaRey May 18, 2011, 10:56 am

        This gives me inspiration…Wendy, has Drew every thought of making short videos or films acting out some of the letters your receive? I think you two could make millions! 🙂

      • Wendy May 18, 2011, 11:13 am

        Thought about it? He talks about it all the time! Alas, I’m camera shy…

      • plasticepoxy May 18, 2011, 11:27 am

        What about cartoons? Maybe that’s too time consuming…

      • spaceboy761 May 18, 2011, 11:55 am

        How about you just handling the voiceover work? The best way I see this working is you acting as the voiceover/narrator while other actors portray what’s going in the letter and proposed response.

      • ReginaRey May 18, 2011, 1:20 pm

        Totally agree! I volunteer to be an actress.

      • Hana May 18, 2011, 1:24 pm

        Me too!

      • spaceboy761 May 18, 2011, 1:30 pm

        I also know a woman in NYC with a ton of voiceover experience. She’s also a 34-year old redhead if serendipity is your thing.

      • Wendy May 18, 2011, 1:37 pm

        Voiceovers I could do (I did them professionally in a another life, actually…); I just hate being on camera. I’ve tried to make a few videos for the site, and I just cuh-ringe watching myself.

      • SGMcG May 18, 2011, 1:54 pm

        What if we only saw only part of your body, like your hands typing on the keyboard or petting Miles and Simone between sentences? You mentioned that they’re camera shy too, but if they could be cute enough for a day, you could probably reuse the footage. Could you have your words typed out-appeared on the screen like they do in Sex in the City or acted out as though LW is following your advice? Maybe even a combination of the two?

      • spaceboy761 May 18, 2011, 2:38 pm

        Voiceovers are probably your best bet anyway. It would be pretty dull to have you there reading the letters and responses vlog-style, since the viewer would have nothing new to look at. Having you voice the letters over a recreation gives the viewer something to watch. Of course, the cost and difficulty of production go well above what is entialed by you talking into a webcam, so that’s a consideration too.

        The tone of these recreations could vary wildly from honest to slapstick, so that’s another decision to be made. Of course, if it were up to me who makes jokes out of pretty much everything, I would play the comedy angle during the letters (insane rants, furries, et al) and make the repsonses more honest since most people writing won’t enjoy being openly mocked with no redemptive advice. It’s tough to maintain that balance between being entertaining and staying true to what you established the site to accomplish.

      • TheGirl May 18, 2011, 3:05 pm

        The ONLY reason I would say not to do it is that I wouldn’t be able to watch it at work. Which is where I am when I do most of my commenting…which I also try not to advertise to my boss.

      • ReginaRey May 18, 2011, 3:56 pm

        Ha! Yeah, my boss praises my work almost every day. If only she knew how capable of multi-tasking I truly was…

  • ReginaRey May 18, 2011, 8:23 am

    I’m so perplexed by this…why couldn’t he have just said, “Have you been going out with other people? Because I have.” That would have probably accomplished the same goal. The fact that he “didn’t want YOU to be hurt” gives me the feeling that he almost wanted to have some sort of power over you, to make you feel insecure or like he was some “hot commodity.” I also get the feeling that if you had answered, “Yes, I had sex with someone else this weekend too, now that you mention it! What a coincidence!!,” he probably wouldn’t have been too cool with it…the whole thing reeks of double standards.

    This guy is at best pretty damn immature and socially uncooth…at worst, he’s really creepy. After 4 dates, there’s no reason to stick around. You have nothing invested, and be glad about that!

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    • melikeycheesecake May 18, 2011, 10:36 am

      I agree that it feels like he wanted her to feel like he was “some hot commodity”

      This guy is a creep and full of red flags. She should be glad she only wasted 4 dates on him.

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  • PFG-SCR May 18, 2011, 8:26 am

    While I agree that he went about this in the wrong way, he seems like he was feeling guilty about it and didn’t really know how to handle it. I think he was probably hoping in some way that she would have done the same, and it would have lessened his guilt a bit. I don’t know…but, nothing else that he’s said or done has been creepy per the LW, so I’d probably not be as harsh on him.

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    • LTC039 May 18, 2011, 9:38 am

      You know, that was my first thought as I was reading the letter…I definitely believe that’s another possibility. We don’t really know the guy, we only have the LW’s side…Maybe he did feel guilty because he really liked the LW…I just think the approach was all wrong…He def. lacks social skills.

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    • LTC039 May 18, 2011, 9:39 am

      Oh & also that he slept with someone the same weekend…that would’ve creeped me out too…

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    • Budjer May 18, 2011, 9:59 am

      Good point. I would say he may not have led with that question if he knew the LW wasn’t going to care about it and I agree that he was grasping at straws hoping she was “guilty” of the same thing he was. A lot of people can say things that can have various interpretations of motivation when in reality it was just an awkwardly executed conversation to rid himself of guilt with no malicious intent.

      There is also a chance he wanted to air this out to avoid another letter to DW 9 months from now consisting of an ex-gf asking if she should forgive her ex-bf for hooking up with someone the same weekend they first hooked up during casual dating because a mutual friend told her about it. Obviously the LW didn’t care – but he didn’t know that and a lot of people would be turned off if someone they were getting to know hooked up with someone else.

      While it’s a little tacky to be lamenting about past woes I can also see how he was trying to convey a reason for bringing up the conversation in the first place with vaguely bringing up bad girl experiences in the past. A few consecutive run-ins with head gaming women can make you a little weary, but he should stop thinking of himself as a victim, be smarter, and not assume every woman he’s getting to know plays games.

      I would recommend the LW being upfront about what she’s feeling and give him a chance to explain himself…and if he isn’t convincing enough then at least she will have the satisfaction of making him squirm a little bit before dropping him for being an intentional d-bag. A candid conversation may be all that is needed.

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  • Desiree May 18, 2011, 8:38 am

    Based on letters in the past, I could see how (had they ended up becoming a permanent item) he might have been afraid that she would find out about that sexual encounter and hold it against him. Having said that, it doesn’t quite sound like he was playing defense here. It sounds like manipulation. And if it isn’t manipulation, and he was being sincere, then he hasn’t evolved very far in terms of communicating with females. Which might explain how he has been “hurt” by women in the past. This reminds me of an odd situation in my past. I was considering becoming intimate with a guy, but I wanted him to be tested for STDs first (I was a virgin; he was quite experienced). He said his test results came back clean. Knowing that there is an incubation period for viruses, I asked him how long ago since he had sex with a girl. He replied, “Last night.” I appreciated his honesty, but let’s just say it didn’t work out between us. Our views of intimacy were too different.

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  • WatersEdge May 18, 2011, 8:43 am

    You’re right to think that this guy reeks of immaturity, manipulation, and a general mistrust of women. Get the hell out of there as soon as possible. Yuck. Wendy is right, he could have found a mature and vague way to ask you if you’re seeing other people without giving you the mental image of him fucking you one day after he fucked someone else. I do think it was poor form for him to sleep with both of you, but technically you’re both still single so I’m glad that you were mature enough to see past the non-infidelity to the underlying, disturbing behavior of telling you and testing you.

    I think you probably passed his test with flying colors because your response to him in that moment was dead-on!

    I think you should send him a link to this page to dump him. That’ll get the message through!

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  • Mainer May 18, 2011, 8:52 am

    Errr, don’t say what Wendy suggested. I know she was just joking, but in case you didn’t pick that up, don’t. I agree this guy may be a little immature or insecure. Maybe it is because of a lack of experience, maybe his confidence has really just been crushed in the past. Either way, he’s not right for you. I think his intentions (in his mind) were nobel (in wanting to confess about sleeping with someone else, perhaps to relieve some guilt), but he did go about it totally wrong. Perhaps (as Desiree mentioned) he is just poor at communication and didn’t know how to bring up the issue, thinking that asking you would be a good segway. Whatever it was, you two are just different. Don’t go down to his level and give some mocking explanation of why you don’t want to keep seeing him. Just cut it off. If he insists on you honestly giving him a reason, which he may, then do as he did: be honest. But always take the higher road and maintain your composure, even (if not especially) within the confines of someone of lower standards. Just because he’s a little off doesn’t make him any less human, and making him feel like shit isn’t going to help his low confidence or faith in women. I don’t know, maybe help him LEARN something about dating etiquette so he gets better? But something tells me his past is filled with nasty rejections that didn’t really teach him anything, and one more is not going to help.

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    • Desiree May 18, 2011, 9:10 am

      I definitely agree with you on her taking the high road. I have been approached by some nice guys who (bless their hearts) were just *really* dumb when it came to dating. Back then I didn’t handle it so well, because I was young and dumb at the dating game as well. I try to be better about it now. I’ve seen too many guys get really bitter about women being awful when it was just that they were using a terrible pick-up line or their cologne smelled horrendous.

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    • WatersEdge May 18, 2011, 9:25 am

      I would like to respectfully disagree that he probably had noble intentions. He said out loud that he was telling her in order to test her. He told her something potentially hurtful with the intention of seeing if she would react dramatically. That is not innocent or noble.

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      • Mainer May 18, 2011, 9:40 am

        I think if that is all he had said, then I would totally agree. But his first rationale behind the whole confession was with ” [I] wanted to be honest about it so [you] wouldn’t be hurt.” Then followed up with, “and I wanted to see your reaction.” I think that second part, again, just boils down to poor communication skills and bad dating etiquette. That is the whole point of dating before we commit to someone, we want to see how they respond to our proclivities. Not to say that him sleeping with other women was going to a common occurrence, but perhaps he just wanted to gauge her views and how she responds to a potentially shocking piece of info. We do this all the time. We obviously tend not to *verbalize* the fact that we’re doing this (which is where the poor social skills come into play), but it happens nonetheless. If I tell a date I have a dog, I’m not only doing this to share something about myself, I’m also doing it to see how she responds. If she tells me she hates dogs, I have a pretty good idea this may not be the most suitable relationship to pursue.

        So whereas him verbalizing something we all do on a day-to-day basis is kind of a stupid and awkward thing to do, I’m not entirely sure is was out of pure manipulation. But again, we have limited info to go and I’ve never met the guy, so who knows.

      • WatersEdge May 18, 2011, 9:45 am

        But his logic is flawed! He was telling her so that she wouldn’t be hurt? I don’t tell people things that they have no need to know and would never find out if I didn’t tell them… so as NOT to hurt them. Why would I? If he didn’t want to hurt her he would not have been so explicit. I think he did want to hurt her and he did it to see if she’d blow up and act like a crazy girl.

      • WatersEdge May 18, 2011, 9:46 am

        AND I think there’s a certain type of person who likes to get a reaction out of people out of an insecure need to see where they stand with the person, and he was doing that. But that’s just my opinion.

      • Mainer May 18, 2011, 9:54 am

        Oh sure, anything is possible. Based on the letter, this guy is one of two people:

        – A manipulative douchbag who likes having the upper hand and wanted to hurt her so he could feel better about himself and get some validation. Or;
        – An inexperienced social-moron who spits out whatever pops into his brain without thinking about it.

        It’s tough to tell from the letter and we can make guesses about his motivations all we want. I guess I was just giving him the benefit of the doubt that he was being honest and wasn’t trying to hurt her.

      • WatersEdge May 18, 2011, 9:57 am

        Ok, fair enough. 🙂

      • TheGirl May 18, 2011, 10:08 am

        Either way, I’m not sure I’d want to date him… sounds like way too much work!

      • WatersEdge May 18, 2011, 12:12 pm


  • spot May 18, 2011, 9:03 am

    “You’ve been hurt? Aww, welcome to life, little guy!”

    HAHAHA so true!!! People pull that card way too much to justify what they know would be considered socially awkward/weird behavior if they didn’t justify it with that.

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    • Rachelgrace53 May 18, 2011, 11:47 am

      So sorry for thumbing you down! What you said it so true! Damn iPhone screen…

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    • MsMisery May 18, 2011, 11:48 am

      “Aww, welcome to life, little guy!” made me literally LOL in my cubicle.

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  • LTC039 May 18, 2011, 9:06 am

    Yupp…this guy sounds tactless & gross…Thank God he revealed himself only into four dates. On to the next one! As Jay-Z would say!

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  • BoomChakaLaka May 18, 2011, 9:10 am

    Yes, definitely immature and you should definitely MOA.

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  • Amber May 18, 2011, 9:10 am

    Wendy, you rock!
    I’m glad you’re back!

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  • cdobbs May 18, 2011, 9:21 am

    ick, what a loser. i hope you have already MOAed, because this guy is not worth the time!

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  • kerrycontrary May 18, 2011, 9:32 am

    LW, you are not being too selective at all! In fact, I think you are being perfectly selective and I would take all of his actions as a bad sign. I would hope that more people who write into Dear Wendy would be as astute and mature as you. Given your description of this guy, I think that there could be more weird problems that pop up in the future. There are guys with better personalities out there who won’t “test” you.

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  • spaceboy761 May 18, 2011, 9:33 am

    This guy sounds like a first-class emodouche. Before he even admitted (oddly) to banging around during your second date, the whole “I’ve been hurt by women before” monologue would be enough of a red flag to end it if you’re only a few weeks in. With no indication of either of your ages, that is something I would expect out of a 19-year old. I guess if you’re both 19ish, it’s par for the course since that age is typically an emotonially wrenchy bangfest anyway.

    On the plus side, vintage pachinko machine? Rock!

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    • WatersEdge May 18, 2011, 9:49 am

      I vote emodouche too. I’ve dated guys like this before and it was a total shitshow.

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      • MsMisery May 18, 2011, 11:55 am

        Actually I think I am going to have to appropriate the term “shitshow” into my regular vocab…

    • Maracuya May 18, 2011, 10:03 am

      I want a vintage pachinko machine, too.

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    • TheGirl May 18, 2011, 10:10 am

      emodouche! I am totally using that one.

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    • leilani May 18, 2011, 10:27 am

      Seriously! The “I’ve been hurt before” thing is such a cop out. I don’t care what’s happened in your past, I still expect the same amount of respect and commitment that I would expect from anyone.

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    • SGMcG May 18, 2011, 11:16 am

      LOL – emodouche! Sounds like some animal you’d encounter in the dating jungle:

      “Now this is the emodouche, biggest of all dating snakes… woooo! He’s smart! Oh! Oh! So funny. Look at that specimen. Crikey! You can tell he’s feeling vulnerable today. See how he tells you ‘I’ve been hurt by women before?’ That defense confession is merely the rattle as he strikes with his venomous test death spiral.”

      The Date Hunter with Spaceboy…yeah, I’d watch that. 😀

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      • spaceboy761 May 18, 2011, 11:27 am

        I already own a tranquilizer gun, so this could work!

  • fast eddie May 18, 2011, 8:37 am

    It was thoughtless of him to the point of being stupid and you can tell him I said so. That said it also opens a candid conversation about sex which is easier to do then to talk about. Turnabout is fair play, ask him to meet for lunch and lay it on him. Hold back on anything you don’t want others to know. Just like in the tabloids, titillation spreads like wildfire.

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  • leilani May 18, 2011, 9:49 am

    Yeah, to me this guy just seems like he thinks he’s hot shit. What be the purpose of specifically telling you that he had sex with someone else the night before he had sex with you besides trying to make you jealous? And asking you if you had sex with someone else on that particular night, when chances are the answer is probably “no” even if you are seeing other people in general, seems like it was just a way for him to get the upper hand. Like other people have said, if his motives were as he said, he would’ve just asked if you were still seeing other people. Even if he brought up having sex with other people, I can’t imagine he would bring up specific times or experiences unless he wanted to make you jealous. This guy seems really immature.

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    • spaceboy761 May 18, 2011, 9:59 am

      I think that accusing this guy of playing the jealousy card might be giving him too much credit. It’s possible that he actually thought this was the right thing to do or (this is my bet) created drama for drama’s sake because he hasn’t yet learned how to distinguish intensity from love. He can’t mentally separate the two.

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      • spaceboy761 May 18, 2011, 10:13 am

        Basically, if you could isolate the reason why 15-year old girls cry their eyes out after breaking up with their boyfriend of three weeks.. that. This guy’s immaturity or lack of experience doesn’t leave him that far removed emotionally from the mindset of that 15-year old girl.

      • melikeycheesecake May 18, 2011, 10:43 am

        @ Spaceboy.. completely agree with your 15-year old response!!! It’s so true! I can laugh about it now… but man at one time I was that 15 year old girl crying her eyes out! Ahhhh the good ole days.:)

    • Maracuya May 18, 2011, 10:02 am

      Yeah, I was thinking this. He could have said, “Did you sleep with anyone while we’ve been dating?” or “Have you been seeing other people?” Instead he just asked a question that, like you said, was more probable to be a ‘no’ just so he could answer, “Oh, that’s so funny, because I did! I’m so popular.”

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    • leilani May 18, 2011, 10:04 am

      It is possible. I might be being too hard on him….I’ve had some experience with some lame guys that would definitely pull this card to make me feel like they’re a hot commodity. Either way, I think this guy seems really immature and not the best guy to get into a relationship with.

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    • LTC039 May 18, 2011, 10:35 am

      I wonder if he had one of the stupid smirks on his face as he was telling her…Like “I’m so sorry to inform you that I women just constantly want me…”

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  • BecBoo84 May 18, 2011, 10:21 am

    Wendy, I love the break up line you gave her. Awesome!

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    • melikeycheesecake May 18, 2011, 10:46 am

      I disagree. Yes it’s hilarious to us… but would not be a good idea for this guy… she might set him back lots more… relationship wise. LW needs to act mature if she decides to MOA.

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  • TheGirl May 18, 2011, 10:21 am

    Either he’s a social moron, an emodouche (credit to spaceboy for that one) or just a total jerk. Any way you slice it, he sounds like too much work. I know all relationships entail some work, but I prefer dating people that don’t need to a smack to the back of the head every four dates. I say give him his verbal smack for being a dumb ass and move on.

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    • Desiree May 18, 2011, 11:02 am

      “I prefer dating people that don’t need a smack to the back of the head every four dates.” Love this! I’ve dated guys like that, and it’s exhausting. Why must I explain that you buying your ex a $100 birthday gift a week after not getting me a Valentine’s Day gift “because of money problems” is hurtful? *Smack* (That was a real scenario. Stupid high school relationship.)

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  • convexed May 18, 2011, 10:44 am

    I’m the LW—he and I are both 25 years old. I’m grateful for all the comments and advice!
    I will say, in response to a few comments, I honestly am not bothered by his ‘extra date’ in the weekend. I’m relatively self-aware and if jealousy or hurt feelings were the case, I would be writing in about that. Many of your comments echoed my impression that he wanted to get the upper hand or boost his sense of desirability. Some of my friends said to give him the benefit of the doubt, that he really just wanted to ‘spare my feelings’, but he certainly didn’t give me the benefit of the doubt in running me through some ‘psycho-bitch-elimination test’!

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    • demoiselle May 18, 2011, 10:56 am

      I’d be careful of anyone who is “testing” you that way either. Someone who is already pushing boundaries, making you uncomfortable, playing power games, and only afterwards informing you that it’s a “test” because he’s been hurt by women before–and you have to constantly prove yourself according to his secret standards–is not someone you want to be involved with. At best he’s unbelievably gauche and sort of unkind. At worst, he’s a potential abuser who will have your head spinning trying to anticipate his games…

      Good luck, and congratulations on getting a clear warning from this jerk early!

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    • spaceboy761 May 18, 2011, 11:01 am

      If this guy is 25, then this is just sad. Tell him to start cruising the bowling alleys for high school chicks and maybe he’ll shack up with somebody on his emotional level. I checked out the website for registered sex offenders and somebody really needs to class up that joint anyway.

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      • demoiselle May 18, 2011, 11:08 am

        Please spare the high school girls. They have enough problems already with immature, jerky older men pursuing them and messing up their lives…

    • SGMcG May 18, 2011, 11:35 am

      o_O Did he really call it the ‘psycho-bitch-elimination test’? Can we say misogynistic emodouche? Don’t just MOA LW, run FAR away!

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    • WatersEdge May 18, 2011, 12:15 pm

      You generally don’t want to date anyone who says things like “All my ex-girlfriends are crazy”…

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      • thyme May 18, 2011, 2:39 pm


    • SpyGlassez May 19, 2011, 1:15 am

      Yeah, I don’t see how this was supposed to “spare your feelings.” If you hadn’t had the exclusivity talk, then it was basically all above-board. There are other ways of letting someone know you aren’t ready to be exclusive (i.e., by saying, I like you but I am not ready to be exclusive). He wanted to prove something, and he wanted to make sure you weren’t going to shriek like a banshee about this; awesome. So he didn’t trust you enough to talk about it like an adult; he chose to turn it into a mindgame. I agree; if you stay then he he will probably do manipulative douchey things in the future. Otherwise, MOA.

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  • Lindsay May 18, 2011, 10:48 am

    I agree with Wendy. This guy is obnoxious on so many levels. Testing someone like that is ridiculous. He obviously didn’t want to know whether she had slept with anyone, so he should have just been straightforward (yet polite) and said that he was still seeing other people. And his reasoning that he doesn’t like “girl behavior” and wanted to see how she’d react is rude. I imagine the “girl behavior” he’s referring to is when girls get angry at him for his bad behavior, and he doesn’t like it. MOA!

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    • MsMisery May 18, 2011, 11:58 am

      That’s what I was thinking! “I’ve been hurt before” probably translated to “Girls constantly dump me because I yank their chains.”

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  • sarolabelle May 18, 2011, 10:52 am

    Maybe I’m different but I see nothing wrong with what he asked her. Sex with other people isn’t something that comes naturally easy to talk about with practical strangers.

    He would most likely would say to her: “hey did you have a dog when growing up?” Then she would say yes or no and you know what he would say next? “Oh, I asked because I had a dog when I was growing up. His name was Scruffy.” It’s the way my bf makes conversation and it just may be the way this guy does too. Give him a break!

    In my honest opinion LW you should be more worried about this line in your letter: “and doesn’t like what he sees as annoying general patterns of girl behavior in relationships” What does that mean? Does he even like women? We cry, get in bad moods, etc. If he doesn’t like annoying general patterns of girl behavior then I don’t think he’ll make a good mate for long.

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  • sobriquet May 18, 2011, 1:35 pm

    Ickkkk. Subtle creepiness is the WORST. The ones who seem awesome most of the time and then that creepy little comment slips out. Misogynistic comment aside, the man who says he’s been hurt before (eye roll) and is therefore wary of women (double eye roll) is not someone you want to enter a serious relationship with. Every fight in the future will revert back to him accusing you of hurting him and leaving him “LIKE ALL THE OTHERS!” because you’re a mean, terrible woman.

    And the test… another huge fail. Why does he feel the need to broadcast the exact weekend he slept with another woman? It’s one thing to say that he’s been sexually active with someone else, it’s another thing entirely to tell you the exact fucking day he had sex. Sorry, this just really bothers me.

    I’d say you have plenty of good reasons to move on.

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  • DebMoore May 18, 2011, 2:38 pm

    You know what? The fact of the matter is he annoyed you. Move on! You can’t be with someone who “annoys” you so quickly into the relationship. I personally can not be with someone who annoys me on a regular basis. Sure my husband does annoying things here and there, but they don’t bother me too much. (he feels the same about me) He and I even joke to our single friends that the key to a long term relationship is to find someone who’s “shit you can put up with”. Everyone is annoying, but as long as their crap/issues doesn’t make you like them any less (like, not love, you can love people you don’t like) then your chances of the long haul I think are much better. I think lots of people are with other people who “annoy” them but gosh darn it they love them, so they put up with it till they can’t anymore. To make a long-term relationship to work you have to like and admire the person you are with at least 90-95% of the time. Just my two cents.

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    • Quakergirl May 18, 2011, 2:51 pm

      Could not agree more. I always say Quakerboy and I get along so well because “he understands my crazy and I understand his,” i.e. we know we both have annoying/bizarre habits and quirks but accept that you can’t pick and choose personality traits– a person is a whole being, and it’s all their traits (both wonderful and irritating) that make them who they are. If you can accept that whole person, and they’re still your favorite person even when they drive you up a wall, then you’re good. If you can’t, move on!

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  • anna728 May 22, 2011, 9:13 pm

    This letter is full of plenty of reasons to ditch this guy, and you don’t sound too invested anyway.

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  • Snoopy June 11, 2019, 11:19 am

    what if the situation is slightly modified? i recently had an incident where the guy and i made out. Oral sex wasn’t involved but we did touch each other’s neither regions with our hands. Then he fixed up our second date two weeks later ; citing excuses of travel and work. while on the second date he casually dropped how “within two days of meeting you, i met another girl. You know what, she started kissing me and we made out .” when i asked if it led to sex? or did he take her home? he said “no, home is not for everyone”—apparently , he had taken me home. Then he said a makeout in public is just kissing; it has no meaning. I really dont know what to make of tis incident or this guy or to continue meeting him.

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