15 Red Flags You Should NOT Ignore

financial-planner-red-flagWhether you’re in a brand-new, not-even-defined-as-of-yet relationship, or you’ve been together for a while, there may be warning signs that all is not rosy and you should MOA. Based on many forum threads, former columns, personal history (my own as well as people I know), here are 15 red flags you should absolutely, positively, definitely NOT ignore if you see them waving in front of you.

1. He’s your boss and he’s married. Enough said.

2. The first time you invite him over to your home, he criticizes where you live (your decor, the location, the neighborhood, the home itself).

3. He says he’s in an open relationship, but, when you ask you meet his significant other, he has 1,001 excuses for why you can’t.

4. He’s married and still lives with his wife, but he says he has “one foot out the door.” Nope. Unless he’s legally separated and living separately from his wife, he is not emotionally available for a relationship. “One foot out the door” is code for “I’m a cheater.”

5. He freaks out if it takes you more than a few minutes to respond to his texts.

6. He asks for details about your sexual history. It is NONE OF HIS DAMN BUSINESS. You owe him nothing but an admission to any STD you might have that you could potentially put him at risk for. If he wants details AND he criticizes you about them? RUN!!!

7. He contacts you on FB or Tinder or Snapchat or whatever the kids are using these days to try to virtually hook up weeks after his divorce is finalized. Maybe you went to HS together a million years ago or share a mutual friend or two. He tells you he was checking out the “people you might know” column and saw your pretty face. Oh, and by the way, his marriage just ended. That’s code for: “I feel emotionally vulnerable and lonely and am looking for a rebound/someone to make me feel better about myself.” Don’t pass go.

8. He uses your body for sexual gratification while you’re sleeping or otherwise not in a position to give consent. OH, HELL NO.

9. You’ve been “dating” for months but have not actually met in person yet and, oh yeah, he doesn’t even really have time to call you anymore because he’s just so busy with his “new job.” You’re not dating, and it’s not a new job that’s keeping you from talking. Home boy has another woman (or women) on the side or JUST ISN’T INTERESTED. In any case, MOA.

10. You meet him in person and discover he’s clearly using outdated photos in his online dating profile that are more flattering than what he currently looks like.

11. He and his sister use the bathroom together, he walks around her naked, he tells her she’s beautiful, and he asks if you’ve ever fantasized about your brothers in a sexual way. RUN. (I deleted the letter, but this is the column that inspired this particular red flag).

12. Your new wife treats your daughter like shit and refuses to go to family counseling even though that’s the only way your daughter has agreed to move back in with you. Fuck that noise.

13. He has multiple personalities that regularly make appearances, and for which he has not sought psychological treatment, and which he didn’t warn you about before driving alone with you into the desert one evening shortly after you started dating.

14. After you go out with him once, he changes his online dating profile to read: β€œI can appretiate nice boobs and booty so I will check out girls with you,” and β€œI like watching horor movies and porn, usually in that order.” Nope. First date is his last date with you. Buh-bye.

15. She teaches tennis to a wealthy, older, married guy despite not really being a tennis teacher or even a very good tennis player.


  1. This made me laugh. It’s fun to see all those random red flags next to each other.

  2. Avatar photo something random says:

    Oh the memories πŸ™‚

  3. I was totally laughing/smiling while reading this. LOVE!

  4. Avatar photo Boobs Magee says:

    I’d also add that you should RUN, not walk, to the nearest exit if you find out your boyfriend (that you just got back together with, btw) is badmouthing you and still sleeping with a so-called ‘psycho’ ex. *facepalm*

    1. Christ, what a douche canoe.

  5. Unwanted_Truth says:

    I call bullshit on number 6, sorry. I think I’d like to know if the person im seeing has ever been involved in a threesome, orgy, or anything of the like. That may be other people’s cup of tea, but it isn’t mine and I’d immediately go away and not be with someone who potentially was both having intercourse and sucking someone off at the same time. No thanks, i would want to know who i am dealing with here. The rest, i agree.

    1. Avatar photo Addie Pray says:

      16. He’s “Unwanted_Truth” from Dear Wendy! (Kidding, kidding, no one can take a joke around here geez.)

      1. Avatar photo mrmidtwenties says:

        bahahahahaha, I don’t know why someone’s previous sexual history would impact whether you would date them now @unwanted_truth. Maybe they were in an orgy but no longer want to be an orgies, so what does it matter? Like Wendy said, as long as they don’t have any STD’s that they can pass to you, who cares?
        @AP, I still haven’t decided what to do for my lady for Valentines Day, but I may ask her if we’re girlfriend and boyfriend, I feel we should decide that.

      2. Avatar photo Addie Pray says:

        I’m just happy you’re going to do something! Sending flowers to work is easy, classy, and zomg women love it.

      3. Avatar photo mrmidtwenties says:

        Flowers to work are out, as she is a teacher, and they don’t let those kind of things get delivered during the day at school. But we are going to a country bar that night to watch all the single people, it will be hilarious.

      4. Good call. Flowers delivered to school in front of students is…interesting…to say the least. I’m speaking from experience. Super duper embarrassing.

      5. Anonymous says:

        Lol hey it’s all in good humor πŸ™‚

    2. Anonymous says:

      Totally agree, Unwanted Truth! I’ve asked every boyfriend about his sexual history early on, and I’ve shared mine. Based on my friends’ experiences on this subject, it seems that kind of discussion is common. For some people, this is important.

    3. Totally agree, Unwanted Truth! I’ve asked every boyfriend about his sexual history early on, and I’ve shared mine. Based on my friends’ experiences on this subject, it seems that kind of discussion is common. For some people, this is important.

      1. Breezy A.M. says:

        I ask too, but probably for the opposite reason of you two: I have no desire to teach somoene, deal with someone who finds oral strange or unsual, deal with someone who doesn’t have an extensive repetoire from which to choose, and I definitely don’t want to be slut shamed. I also don’t want to get into the nonsense I’ve seen too many times where friends would marry and then after a decade or so one of them decides they missed out on having lots of fun sexual adventures and their marriage either goes to crap or they split up or go open (and it’s rare I’ve seen that NOT end in eventual divorce). So when I am getting to know a guy and he says he’s only had 3-4 partners, or shows he thinks some sort of sexual act is wrong/dirty (by design, not just his preference) I know I need to MOA!

  6. HollyMarie says:

    #17. He constantly badmouths his ex, calling her a “bitch,” “psycho,” etc. Sadly, this one shows up in way too many letters and forum postings to link to.

  7. This was a fun read, but I was hoping for less obvious tips! πŸ™‚

    1. Avatar photo Addie Pray says:

      Here are some tips I’ve learned from personal experience:
      1. He yells at his 90 year old grandmother;
      2. He refers to all his exes as bitches;
      3. His words and actions don’t align;
      4. He invites you to his family functions and friends outings and whatnot but doesn’t express interest in meeting your family or friends;
      5. He hates your puppy.

      1. oh my!

      2. Ruh-roh πŸ™

      3. What kind of monster hates puppies?

      4. Avatar photo Addie Pray says:

        i know!!!

      5. 6. He calls his niece a cunt. Yes that happened. And there was no 2nd date.

      6. Avatar photo Addie Pray says:

        Really? Are you sure he didn’t say a runt? Because maybe she’s really small?

      7. Absolutely positive. Pretty good date actually until I heard him say that.

      8. What, no?! No one can hate Moose! What kind of monster?!

  8. Shouldn’t there be a link for #13?

  9. Coincidentally, I was just googling about red flags to watch out for the other day. These are original though, great idea to use the posts by others in the past weeks.
    However, I do think for some people sexual history is important (depending on religion or how conservative they are etc.) I’d get put off by someone who’s had like 50 one night stands in their first year at university/college, for example (apologies if I’m offending someone with this, not intended, personal opinion). And I have known cases where this exact thing has made a huge negative impact on relationships and the person wished they’d asked their partner much earlier on.

    1. Eh when you think about it, 50 one night stands in a year isn’t really that much. That’s like one a week. I don’t think it’s that outrageous or uncommon. People can have whatever standards they want about their own sex lives, but I don’t think putting that on others is not okay. Like my husband was very conservative about who he chose to sleep with, but could care less I had very different behaviors.

      1. Well, I respect your opinion. That is *your * opinion and I personally see things very differently. I know it’s not uncommon at all to sleep around with different people every other night, I don’t judge my friends for doing it, not at all, But this just goes against my own values and does definitely change the way I view a potential partner, someone I am committing to being in a relationship with.
        That’s just me, no hate please πŸ˜‰
        The world would be boring if we all thought and felt everything the same way anyway.

      2. I’m curious how you would react if someone you were dating was unwilling to share their sexual history with you? Personally I don’t think it’s so much that curiosity about a partner’s previous experiences is not warranted, it’s more that people have a right to privacy about aspects of their personal history they don’t want to share and in the end you won’t know if you’ve been told everything anyway.
        Plus, I would say that you can get all the important information from what someone is telling you about their current intentions: If they currently want to be monogamous and have certain sexual preferences, how does it matter that in the past they may have been promiscuous and into different things?
        This is what cracked me up about “The Unwanted Truth’s” original comment, the idea that someone would “potentially both be having intercourse and sucking someone off”. I mean, what’s the “potentially” there… The fact that someone once had a threesome means they’d do it again? How is the mere “potential” to be having sex with two people at once even relevant unless it is believed that such experiences show a lack of character or something? Because I can’t really see any other motivation than trying to infer stuff about character from sexual behavior I tend to give the side-eye to investigations into a partner’s sexual past.

      3. Agreed. I’d be way more concerned if they wanted to try it and hadn’t. If someone had tried out all these other things (and people) and knew what they wanted, I’d think that would make them a better partner than someone who had all these unfulfilled what if’s at the back of their mind.

      4. That’s true, I hadn’t thought of that possibility. Generally I think that past sexual history is sort of overrated. Like, I’ve never felt that it affected any of the relationships I was in. I think that’s true whether it’s with someone with a lot of sexual experience or not much sexual experience at all. Basically if you can create a fulfilling sex life with someone in the present, past experience are not going to matter much.

      5. That’s just how I feel about it..
        I haven’t encountered so far the case where a guy is reluctant to share his romantic or sexual experiences with me. I wouldn’t expect him to share this with me in the first month of dating (and I don’t share these things that soon either, it *is* something personal). But I do believe that if you’ve been going out with someone for, for example, 2 years, let alone if you’re planning on getting married… I don’t know, to me at least it seems like a pretty normal thing to share with your intimate long-term partner. I don’t mind sharing my past with someone I trust and care about and none of the guys I’ve dated seemed to care about sharing this either.
        Honestly, I don’t know how I’d respond if a guy refuses to share his sexual past if we’ve been going out for a couple of years, for example. If he tells me “It’s none of your business”, I wouldn’t like it, I won’t lie. I would probably think he’s done some pretty outrageous stuff which he knows I wouldn’t like. If he told me he’d slept with x amount of women and later I happen to find out he’s actually had x multiplied by 10 one night stands alone, I would feel lied to.
        I find it to be a sign of trust and intimacy to be able to share personal things like this with your partner. Yeah everyone is entitled to their privacy, it’s not like I’m asking for his passwords to read his emails and messages and texts. I also find it funny how you always find people “bragging” about the number of sexual partners they have had in totally casual social occasions to people they have literally just met (I know both guys and women who do this) but when it comes to saying it to the person you supposedly love and care about and are comimtted to, it’s none of their business.

        Again, that’s just me. In all seriousness, I don’t agree with many views people share either online or in real life, I just accept them as they are – differing from mine.

      6. Oh, also the topic which this refers to was about the controlling, borderline emotionally abusive boyfriend who was criticizing the LW about her past, making her feel like a slut and overall a horrible person for having a (not large) number of sexual partners. It was more about the way the boyfriend responded when she shared this with him (controlling and manipulative) as opposed to her sharing it in the first place.

  10. Avatar photo bittergaymark says:

    I think the one thing some women do better than anybody is ignore red flags. There could be five million fucking red flags — and yet some, many it seems, will just endlessly prattle on and on about their “special” love….

  11. He lives with his “sister” but can’t call when she’s home and texts from a free texting app rather than a normal cell phone.

    He details within a week of meeting you how he makes his living embezzling money from his parents’ business which they stupidly let him keep the books for.

    He lives in a cheap motel and is regularly wasted in the middle of the day.

    All true stories…

  12. hobbesnblue says:

    I’m going to play a tiny bit of devil’s advocate on #3. I’m sure that 99.9% of the time, Wendy’s right, and that kind of behavior would be shady as hell. However, speaking for myself, I’m not totally dead set against an open relationship, but if I did give my boyfriend/husband permission to have some sort of FWB situation on the side, I would rather not meet her or feel the need to be chummy.

    1. Avatar photo Stonegypsy says:

      And some people really do have DADT rules on their open relationship. In fact, that’s a pretty common setup.
      I don’t think it’s a great one, but it’s a common one.

      1. Avatar photo Stonegypsy says:

        I also won’t date people in those kinds of setups, though, just cause it *could* be shady, and because people who do have that sort of open relationship I feel like often aren’t ready for one or don’t really want one.

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