Single LadyGuide: 5 Warning Signs that You’re on a Date with a Jerk

My dating life has been rather busy lately thanks to a reactivated online dating profile. Because I have taken many of these coffee dates into boyfriend territory, I’ve developed a list of red flags that let me know if I’m on a date with a jerk. Trust me when I say that 9 times out of 10, ignoring these signs leads to personal misery.

1. He wants to debate. If you read Persephone and are bookish and clever, you probably have strong opinions on many things, and many of these opinions buck the status quo, which is why you love us and why we love you, but if you tell a jerk this, he’ll want to debate, which really means he wants to derail everything you say and prove that he is the smartest, most manliest debater ever.

2. He asks why you are still single. This is a tricky one because it is often framed as a compliment, “Why is a beautiful woman like you still single?” But really he’s about to draw upon any and all stereotypes about single women: you’re picky, you’re batshit crazy, or you think you’re too good for nice guys like him.

3. Related, he says he’s a nice guy. Nice Guy Syndrome sends all of my alarms a-blazing because nice guys are rarely ever good in bed and they are usually horrible human beings. Despite their exceeding niceness, they refuse to listen to you because they are too damn busy pretending to be nice. They also have a tendency to explode the moment you get angry at them, because why would you get angry at someone so nice?

4. He says he’s a feminist and then qualifies it with, “I treat women just like men, because isn’t that what feminism is all about?” People, this is code for, “I am a complete and total mindfuck.” Why? Because it means that dudebro interprets lacks of respect for women as treating them like men, and when he doesn’t call when he says he will? That’s what he calls feminism.

5. He interrupts you. This one is a gimmee, of course, but needs stating because guys who interrupt? Usually jerks.

Sometimes a guy can be a perfect gentleman during a date, but after the date his jerkiness starts to show. The primary indicator here is a guy who says he wants to take you out again and then waits until the last minute to ask you for your second date, leaving you on pins and needles all week. The contrast to this is the guy who obsessively calls and texts you post coffee date – dude, I barely know you and you are acting a little cray-cray.

What red flags lead you to to run screaming for the exits on a date? Share them in the comments.

By [E] Sally Lawton

My food groups are cheese, bacon, and hot tea. I like studying cities and playing with my cat, Buffy.

49 replies on “Single LadyGuide: 5 Warning Signs that You’re on a Date with a Jerk”

Wow that sounds like the profile of every guy I’ve ever dated… It almost makes me glad to be single. At least I’m not still stuck in toxic relationships with them anymore!

Also, to any guys out there: Is there some sort of secret class where you go to learn how to derail people?

Laughing at/dismissing me when I’m trying to talk about something serious.  I was on a date with a guy (not a first date, so we had moved on to slightly heavier conversational topics) and he ended up saying some pretty sexist things.  I tried to call him out on it – not attacking him personally, just pointing out that some of what he said was generalizing and rooted in sexism – and he laughed and made a joke about how much I’d had to drink (I was halfway through my first beer, and I am in no way a lightweight.)  I was FURIOUS.  That was the last time I saw him.

Interrupting is a no whether it’s someone you’re dating or not. Also, in SoCal flakiness is a huge problem. Cancelling last minute, being late or thinking you can schedule a date with less than a day’s notice. I like debaters. My bf and I get into it all the time and I love it. Oh! I almost forgot, limp handshakes make me queasy.

this post kind of bummed me out. i have only been on maybe 5 dates in my life so it doesn’t affect me but i feel like i would break several of your rules.

“he wants to debate” you surely can’t mean you just want someone to agree with you about everything, or to be wishy-washy or not have strong opinions too? you don’t want to be challenged about anything? granted, not in an aggressive or antagonistic “i’m right and you’re wrong” way but if you said you hated a movie I loved, i’d have to ask why, which could potentially lead to a “debate.”

“he asks why you are still single” this seems a bit presumptuous and I would never ask it, but it hardly seems like an indicator of a jerk. the thing that bothers me is the implication that there is something wrong with being single, not that it’s an excuse to label you or categorize your problems.

“he says he’s a nice guy” probably not something i would come out and say but i definitely AM a nice guy, genuinely, and great at sex. maybe there are a bunch of asshole guys out there saying this ruining it for the actual “nice guys” but there are definitely some guys who are just nice, in a non-obsequious, thoughtful, generous, empathic sense of the word. doesn’t seem like a great way to tell if someone is a jerk.

#4 i’d characterize myself as a feminist but that’s not going to stop me from walking on the street side or opening doors or pulling out chairs – stuff i love to do. so when qualified as you described, i’d agree – but it has nothing to do with the feminist part. i’d agree because someone who doesn’t understand feminism at all is probably an idiot.

“he interrupts you” i do this sometimes when i’m having a passionate or exciting conversation with someone. i can’t help trying to finish someone’s sentences. it’s a bad habit but two people interrupting each other and talking over each other when they are in agreement is not the same thing as someone who just blurts shit out while you’re talking. again i think you’re painting with too broad a brush.

i have never dated men but it sounds like you just had a lot of bad luck. i think if you’re breaking things off with guys just because they disagree with you or ask why you are single you’re not helping yourself out.

Hi Joe,

Perhaps familiarize yourself with this post:

Then, take a step back and realize that you are a dude lecturing a woman on what makes her uncomfortable in a partner, even in the short term.  I get that you think that interrupting people might only be part of a spirited converstation, but it also indicates that you aren’t as interested in listening to your date as you are talking at your date.

As for the whole “why are you single?” – it implies that something is wrong with the person that phrase is being used in regard to.  Don’t ever say that.  It is assy.  If you can’t empathize enough with other people to understand that point, I can’t do anything for you.

Finally, “he wants to debate,” is more about the dating partner wanting to change your mind about some point, rather than getting to know you generally.  First dates are not for ‘debate.’ They’re for “hi, I like A Game of Thrones, and you do to! THINGS IN COMMON THAT WE CAN BUILD ON FOR LATER!”





i don’t think i was “lecturing.” that’s kind of a pejorative term and i don’t think i was doing anything wrong. however i get that it was an article by a woman, for women, and my opinions are probably not relevant or interesting to the audience here. fair enough.

all i can say about interrupting is have you never had an enjoyable conversation where ideas and connections flew out so fast that you and your conversation partner were interrupting each other? i get there is a bad kind of interrupting but is there not also a good kind?

i agree with you about the “why are you still single,” i think i made that same point myself. if someone says that to me, i am definitely going to think less of them. but to immediately write someone off as a jerk just for that question? don’t you think that’s a bit much?

and i can’t put myself in the backseat enough to just passively let stuff slip by that i disagree with. maybe it’s a character flaw and i actually am a jerk and don’t realize it but i’ve never been called a jerk by anyone, and my ex girlfriend told me that the best thing about me is that i have “an opinion about everything.”

maybe i’m missing the tone of the article and it wasn’t meant to be taken seriously.  i’m a Nice Guy so i’m insecure and oversensitive (according to that really obnoxious article you linked to) so I probably shouldn’t have been annoyed that according to this list i must be a jerk. in that article men are criticized for not having opinions, in this article men are criticized for having opinions. seems like i can’t win.

Just out of curiosity… did you click on that handy “derailing” link up there? Cause it (snarkily) illustrates quite well what you did in your original comment. But in case you don’t want to click through, I’m happy to sum it up for you (no sarcasm, I’m serious).

Derailing is when people who have living experiences you don’t (like, dating men) explain some of the negative aspects they frequently encountere in such an experience – like Sally did here in her article – and then you decide that their experience is irrelevant/not the way things are because you don’t think so/a small (and therefore negligible) subset of what is actually common, and you dismiss their experience out of hand (which you did, by suggesting that her finding these qualities unattractive was somehow evidence that she had bad luck in dating or was ‘not doing herself any favors’ by rejecting men with the qualities she found undesirable). In other words, because you can’t relate to what Sally said about dating men (though you went right ahead and affirmed her perspective, bullet by bullet), you’ve decided she’s doing something wrong in her dating life, rather than just agreeing with her that yes, she is justified in not personally desiring men who do the things she illustrated.

Sally didn’t just have a lot of bad luck. She had experiences that are common enough that every other person who commented on this article could not only relate to, but could also expand upon. And, when you went down her bullet list, you also had plenty of reasons to illustrate why you yourself would not do the things that she illustrated in her article. So I’m not sure why you felt the need to come up in here and a: do pretty much exactly what Sally illustrated in her first point (debating for the hell of being contrary), and b: miss the chance to hear what is clearly a fairly widespread experience of women who date men – that there are common behaviors some men engage in that are a turnoff for the kind of bookish and clever women who frequent this site. Did you read her whole article? I’m asking seriously, because your debate seemed to be with her bolded phrases alone – your commentary on them seemed to agree almost universally with her illustration of each point.

You seem like a decent guy, to hear you tell it, and I think what Sally – and every woman who commented on this article – is trying to say is that decent behavior combined with respect and a willingness to hear compassionately the other person’s perspective without trying to find nitpicky reasons why they’re wrong is what these women find attractive. You’re under no compulsion to fit that mold, but it’s also a little confusing when you come up in here and try to suggest that Sally (or the rest of us) are doing something wrong by not finding these behaviors attractive.

I think Sally’s helping herself out just fine by identifying behaviors that are routinely unattractive to her, and avoiding them.

you’re 100% right and i was on shaky ground replying in the first place. it’s like a white person telling a black person complaining about racism that “not all whites are like that.” it’s kind of insensitive and not really the place or time for it.

If I weren’t in love and married to the other nice guy on the planet, I’d probably go on a date with you, if only because of this comment you just made right thar–only if you mean it sincerely, of course.

Men (or perhaps people in general) who can recognize an error, apologize for it, and quickly summarize that they understand their mistake are at the very top of the humanity heap, in my book.

That’s pretty much exactly what it’s like. Thanks, Joe.

I am curious, because it was kind of a footnoted issue in your comment but it’s one I’m trying to figure out in my own encounters: can you help me figure out why feminism is somehow aligned with not liking people to observe basic courtesy by holding doors (etc.) for them? I hear it a lot from guys who usually say it in the same context you did: “I’m a feminist but I like to (insert courteous action here).” I’m only confused because I’ve never heard a feminist woman say, “Oh, NO, don’t open a door for me! That’s misogyny in action!” But it seems to be a common perception nonetheless, and if there are feminists out there propagating this oddity, I’d like to know about it. :)

There’s this new buzzword-y rhetorical talking point called “benevolent sexism.”  The idea is that a lot of the stuff that men do for women that’s framed as being polite or kind is really about how women can’t do things for themselves and/or need protecting (OR how men do it better).  Not sure where I fall on the issue yet.

I think I’ve seen both scenarios: ones in which the man is behaving openly condescendingly to me (“I’ll go drive the four-wheeler over here for you; you’re a lady, after all, and we all know what a disaster that might be! Har har har!”) and ones in which the man is just genuinely trying to be nice (“Here, let me help you carry that enormous cart load of bottled water into the house.”)

In the former case, the goal is clearly to make me feel small, incapable, diminished, or foolish–that’s the intention, not courtesy. In the latter case, there may be times where the guys are inadvertently stepping on my toes, but it’s accidentally and with the genuine intention of courtesy. I have more patience for that and unless they’re stepping hard on my toes, I’m happy to accept their offers of benevolence with gratitude for their sincere intentions.

So yeah. I guess I’m with you. I don’t really know what to think of this notion of benevolent sexism, especially when it runs the risk of steamrolling genuinely harmless, good intentioned acts.

Well benevolent sexism is never the first scenario.  It’s a tangent of the larger “nice guy” thing, sort of.  When a guy opens a door for a girl, even when it’s a genuine act of kindness, the fact that men are taught to do this is sexist.  Or something.

IMO, until society changes, I usually think that a guy going out of his way to prove his kindness in these “benevolently sexist” ways is probably the easiest way to tell that he might be legitimately nice.  Dating as a feminist is tough.  If you don’t cave to SOME of the sexist bullshit you end up never dating at all.

wow quite a debate! not sure who to reply to exactly… but I’ve let random guys open/hold doors for me, out of supposed niceness and then caught them checking out my backside… and that makes me excruciatingly uncomfortable. Oh yeah and it’s sexist/misogynistic. Like I didn’t just decide to walk through this door so you could objectify me, I have places to go, shit to do. BLOGS TO WRITE FOR. I am not just a piece of meat and I can open my own doors. THANKS.

Huh. I think Michelle points out examples when it IS sexism, but I think any act of kindness can be tweaked to make people feel small instead of being done out of genuine kindness. I don’t think that’s a reason to discourage people from being genuinely kind or courteous. Besides, it’s not like it’s a MAN’S job to open a door. Whoever reaches it first should open the damn thing and hold it for others – it’s practical!

Well I do think there’s a certain subset of guys who try to prove something with the olde timey “It’s a man’s job to open doors for women and to provide for her!” thing, and that IS benevolent sexism.  But usually it’s just reaching for the sake of writing a blog post or whatever, and it’s the sort of reactionary, over-thought bullshit that gives feminism a bad name.

(Once I wouldn’t let a guy loan me his jacket “because of feminism,” but I [drunkenly] explained that it didn’t make sense and wasn’t fair for him to be cold because I was a moron and didn’t bring a jacket, and when he said he felt bad seeing me be cold I told him he was being sexist. But I was drunk. So I’m just piping in humorously to say that once a feminist DID do that, and she is sorry for giving all feminists a bad name.)

You admit that you’ve been on five dates.  Nothing wrong with that, really.  But do you want to go on more?  Instead of defending your right to do things that we are TELLING YOU WE DON’T LIKE, how about you just stop doing them?  Or keep doing them, and continue to alienate women who aren’t thrilled by this stuff.

Seriously.  This article could bear the alternate title of, “Women Hate This Shit.”  No woman in this post is disagreeing with anything in the article.  Then you come in here and say, “I think you should change your minds and start liking it!”  No.   You can keep doing what you’re doing, and we can keep thinking it’s annoying.

Or when they say something serious that sounds true (“My brother died of cancer” or “I just finished my stint in the army.”) and then you run with that conversation in a very respectful away until he goes, “lol jk that didn’t happen.”  There is absolutely nothing left to say after that.

Being jealous or possessive, especially on the first date! I went out with a guy one time who wasn’t really my type but I might have been willing to give him a second chance. We were riding the bus back to where I was staying, and there was a guy crying at the back of the bus. I was curious and looked back at him a few times. My date started freaking out and asking if I was interested in the other guy. Yeah, I didn’t return any of his calls after that.

If I already know the guy, I take a look at his close circle of friends, particularly any guys that you’re not sexually attracted to.  It’s definitely true that you’re represented by the company you keep, and if the guy you’re seeing has some majorly problematic friends, you’ll usually start to see that pop up in the guy later.

The classic: being mean or dismissive to waiters/service staff of any kind. Instant killer of any and all ladyboners.

Another one of the world’s biggest turnoffs: the undermining compliment. If I hear one of those, I will run a mile. And I hate running.

It works on women who are very young, inexperienced, and who have not been treated well in the past.  They’re vulnerable and need help (not manipulation), but pick-up artists think it’s fun to fuck with their heads.  A woman who has her shit together and is ready for a substantial relationship (ie the sort of woman who has the internal strength and life circumstances that would make her an awesome, low-hassle girlfriend) isn’t going to fall for this shit, although pua’s seem to think they will.

For me, a big one (like Dormouse says below) was those who were inconsistent, but instead of being liars necessarily to ME, I watched the difference between how they treated me (who they were trying to fuck) versus other people (like, waiters and salespeople, or friends behind their backs). If there was an ugly distinction between the two – being dismissive of me but hanging on a dude friend’s every word, or being golden with me and then looking at a waitress like she was a slug – then sayonara.

Inconsistency! If anything the guy says sounds inconsistent, tread carefully. I dated a chronic liar and a guy who would say that he loved me–then spend a lot of time with other friends who were girls and not make time for me–so inconsistency is a big clue to a someone’s character.

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