In hindsight, what were some dating red flags you missed or chose to ignore? Where is the line between giving people a chance/benefit of the doubt and overlooking bad signs?

29 comments

1. Anytime someone invalidates your emotions and then causes you to feel bad about them, it’s a huge red flag. Also the health issues. You downplayed it, but I’m guessing he makes it a big deal. I find that to be another red flag. Everyone has health issues. We choose to either live with it or make it a problem in our life. This sounds a lot like my ex-wife. These people always play the victim no matter the situation. They have an uncanny ability to make you feel sorry for them and to cause you to doubt yourself. Some of the best advice I’ve read is “pay attention to how they make you feel about yourself, not how they make you feel in the moment.” And “What’s your decision when you are thinking the most clearly and go with that.”

2. Given all you listed here, it sounds like this guy was not meeting your needs most of the time. As much as we want to give people the benefit of the doubt (I’ve been there!), if someone isn’t meeting your needs at the start of things (no validation, not matching your effort, canceling, not initiating, not kissing you, not showing excitement, the list goes on…) then there’s no way he can ever meet your needs in a relationship. I think in dating, I’ve learned that you have to assess fit based on how this person is showing up right now, not based on some potential they could have. I know it’s hard but ending it is the right thing here.

3. This was a lot to take in. The first concern for me would have been not trying to respectfully break the touch barrier or kiss you after a few dates. Outside of that it sounds like this guy wasn’t into you and probably was investing in someone else. Also if you’re always initiating conversations, stop. After maybe two times leave it alone. The whole ‘if he wanted to he would’ is real.

4. This guy sounds like he bait and switched you. Seems like a lot of investment from your side when he hasn’t even tried to kiss you. There are a lot of red flags here and he is making little to no effort.

5. One of the main things I am looking for is someone who is enthusiastic about being with me.

   This guy was not enthusiastic at all, cut him loose. He’s waisting your time.

6. Hmm tbh I don’t feel like the relationship played itself out all the way so I have lingering doubts about it but:

   * not being able to voice difficult feelings or ideas

   I dated a guy for a year that just really would avoid any sort of difficult topic as best as he could. Like, for example, if it was something that might hurt my feelings he just wouldn’t say it or kind of outright lie about it (example: early on he invited me to friends party and regretted it because we weren’t yet official and he was worried I’d break up with him – so he told me actually the friends place was too small, or that he had briefly dated the friend hoping I would feel too uncomfortable to go, until eventually he admitted the truth).

   This behavior really unsettled me because I ended up worrying, perhaps needlessly, we’ll never know… that he would change his whole mind about me one day or would, for example, want to change his/our lives in a way that he was certain I wouldn’t like (eg moving away somewhere etc) and he would resent me without even having a conversation

   This was a part of previous relationships too. His long distance ex and him had an open relationship and a don’t ask don’t tell policy. They broke up for other reasons but if I were ever in an open relationship (I mean I prefer monogamy but who knows how I’ll change) I would want to be perfectly transparent with my partner and I would expect that as well from them.

   So yeah – he wasn’t a liar or dishonest habitually… just had this extreme aversion to hurting people but it ended up making everything worse. I understand that’s a common thing but ah it scares me so much lol

7. My last ex had another date lined up for the same evening as her first date with me, cancelled on him with less than five minutes’ warning when things were going well between us, and was baffled when he blocked her.

   It turned out she’d cheated on her last ex, and I got dumped with almost no warning when she reconnected with the affair partner.

8. Wanting to wait to have sex. These people always turn out to be duds.

9. Yeah “relax and enjoy”? This is just a casual situationship to him. I think it’s important to understand that some people will act relationshippy but they absolutely don’t want a relationship. It’s not important to understand their motivations (I sure don’t) but just to know there’s a LOT of people out there who will drag something out for months even though they don’t like you. So move forward with that knowledge and next time you’ll be able to identify it a lot sooner. So sorry this happened to you – my first situationship happened this past year and it’s painful as hell especially when you don’t understand why.

10. I don’t think OP is asking for advice here but is asking for examples from the crowd of similar scenarios where we overlooked clues/flags that would have saved us some time later on when things inevitably ended.

    I have two examples from past dating. The first is an ex that I dated when I was in business school. I had a crush on her during undergrad so when it was 8 years after graduation and we both ended up in the same city and she reached out to me on FB it felt like it was meant to be. I think this “storybook” situation caused me to ignore flags/signs that would eventually be the reason why things ended.

    First sign – she said that she had moved to the area to get away from a relationship in NYC that had ended badly. This was a clue that she wasn’t truly over her ex, but I ignored it.

    Second sign – When we started dating I had already signed an offer to join a company after graduation that was located in the city. She saw what my starting salary was (low six figures) and asked me why I even bothered with business school if this was what I was going to be making. She came from money and her trust fund paid for her college tuition while I was only able to attend our undergrad due to scholarship/grant money due to coming from a single parent household where my dad made decent money (65K) but not overwhelming money. This was a sign that her perspective of money was very different than mine and this played out in the end when she told me that we would never get married because I don’t come from money.

    Third sign – she would constantly talk about moving back to NYC. It was clear that she had no long term plans to remain in the area. I had no desire to live in NYC but I naively assumed we would find a middle ground.

    Fourth sign – she wanted to keep things “fun” and “light” and didn’t want to get too serious. We were in our early 30s when we started dating so I was at a point where I wanted something long term but she had just left an abusive long term relationship the previous year and had clearly not healed. I should have stayed gone the first time this issue came up.

    All of these signs happened within the first couple of months of us dating. There were many other signs such as her not wanting to meet my family or take pictures with us during my b-school graduation (in fact she left early). Bottom line is that she wanted her cake and to eat it too…she claimed she wanted something casual but expected us to spend time together as if we were serious and when I would leave the situation due to us having different wants/needs she would come back around because she was lonely and restart things.

    The second time I ignored red flags was when I dated someone who was an immigrant and was married to her ex for the green card. Ironically it wasn’t the green card situation that ended things. She got her green card and divorced her ex during our relationship. The red flags were her inability to communicate in a healthy way and the fact that she would constantly make promises that she couldn’t keep.

    After that relationship I was very lucky to meet someone who does not have any of these red flags and it is wild to think about how stressed I used to be in those relationships because there was always an underlying conflict. Now, it almost feels surreal to wake up and have every thing just be “good” lol.

11. He seemed weirdly competitive, had zero friends and almost no relationship experience (late 30s).

12. I dated a good friend who was very sweet. We had different worldviews but I thought we’d be able to get past that with solid communication. Nope! Turned into a dealbreaker when conflict arose. You need to be on the same page about what relationships and marriage are.

13. This reminds me of a woman I went out with a few years ago. Met on a dating app, texting energy was there and so I asked her out. 6 dates in the span of a month and I was not able to get any further than a weak hug from her. I tried to initiate a kiss on the last date and she turned away and made it clear she wasn’t interested. I gave up and said never again! If there’s no romantic energy in the first few dates, I’m cutting her loose.

14. * Wanting to monopolize my time (trying to stop by my office when I was at work, in between meetings, etc.) = *a sign of someone who can’t respect boundaries around time and my career*
    * Getting upset when I make innocuous comments (literally, one of our fights was about the weather, he got mad that I compared it to London weather, where I studied abroad. Somehow that was me “bragging”). Then he asked me not to talk about my past travels = *they are a controlling person*
    * Asking me not to talk to my friends about our arguments *= isolating and controlling behavior*
    * Overly critical of my core personality traits (“you are too talkative”, “you’re a passive feminist”) = *again, controlling and asshole behavior*
    * General lack of introspection or ability to proactively apologize and reflect on their own behavior = *things will always be your fault,* *you are the one who will need to bend to accommodate them*

    I could go on but let’s just say I’m very glad we broke up.

15. Some of my favorite red flags from people I’ve dated:

    – No LTR experience longer than a year. This is crucial because it often means our dating styles do not align. But I do let this one go depending on the person’s situation.
    – Recently out of a LTR. Wow, the number of times this has happened to me and blown up in my face is shocking. Also I never learn my lesson.
    – Green text bubbles. I kid. Or am I?
    – Jokes about me paying for the date. I wish I was kidding for this one.
    – Sharing trauma on the first date. This has never gone well no matter who shares it, even with the best intentions.
    – Separated but not divorced
    – Very one sided conversations where I speak one minute for their every ten (or twenty or thirty)
    – Asking me to FaceTime every night before bed
    – Telling me I check all their boxes and then describing all superficial stuff like my job or body type
    – Accusing me of using them for sex and then changing their mind when I suggest having less sex
    – Small easily verifiable white lies during conversations or sex

    Alas this list was longer but I decided to cut it down to something more general

16. There are a lot of good advices in this thread.
    This reminded me very much of my situation. It only ended a few weeks ago so I still think of him/the relationship from time to time. So as to not get into another similar one.

    In the beginning this guy was very active with setting up dates/kissing/hugging etc. And I had no doubt he was interested in me because he would travel about an hour to come meet me. He was funny and cuddly and I liked him a lot. However, there were a few things that didn’t match my effort.
    He wouldn’t text or call me much. It was already 1 month and even then I was the only one to call. He would send me a “have a good day” text and that was it mostly. In between dates there was hardly any communication. Then he went to meet his family for more than a week. No call! And when I told him it would be good if he called me more, he said “But I do call you”.

    I always paid for my food, activities myself, and sometimes also for him but I didn’t think much about it at that time. When I look back, I can’t help thinking that he was maybe after the free stuff..I don’t mind paying for myself, but once in a while it feels good when the guy makes some effort too. Shows that he cares about me.

    Then we went on a trip and he had a toothache. Throughout the whole trip he made such a big fuss about it. It was as if he wanted me to suffer together with him.

    There was no physical intimacy at all during the trip. Even when I initiated it, not much reciprocation. If I asked about it, he would turn the topic around and make excuses. for example, I disturbed his sleep, or that he is too tired, or that he does intiate but I don’t notice. He just couldn’t admit some things.

    Then he told me he was going on a 2 weeks trip with a girl, only his best friend. I expressed my concern and he didn’t do much to assure me. He could see that I was upset but he would just leave me behind and walk alone wherever we were.

    Even after two months (we were still on the trip), when I asked him where our relationship stood, he said he still needed time. But during the trip he had his birthday (and I took him for dinner to a restaurant of his choice) but he mentioned later that I didn’t put a lot of effort into making his birth special! This was all after saying he wasn’t sure about our relationship, after not giving me enough assurances about his other girl friend and the trip, after letting me get upset so many times and doing nothing about it, after not giving me any physical affection and instead yelling at me when I asked or begged for it! So many signs..And I feel stupid about it now.

    So yeah, I kept giving him benefit of the doubt again and again. I am so glad it only lasted 2 months. Even though it cost me a lot of emotional and some financial effort, I am quite glad that it ended and that I learned my lesson. I hope I can recognize the signs early next time.

    Like the other posters said, try to recognize what you feel when you are in a clearer state of mind. Deep down you will know what is not going right..

17. She abandoned all of her friends.

    I witnessed one long-term ex drop her friends a few times. The first was around when I met her she mentioned that she didn’t care to know her HS friends anymore. She did the same thing a few years later with some old work friends that she’d known for years, just cut them off. Then when we were on the rocks and breaking up after several years she made a point to tell me I could keep all of our dozens of mutual friends that we’d met in university. She never spoke to any of them again. That’s nuts to me.

18. Two of my keys are that someone makes me feel safe and that I always know how they feel about me. This guy did neither. You admit that he made you act out of insecurity and that you didn’t know how he felt about you. Time to stop investing in him.

    A huge red flag I ignored with a guy a long time ago was that he spent the whole first date trauma dumping. I know now that he was trying to create a false sense of intimacy. He also was totally unwilling to come to me (I lived 30 minutes away) or usually initiate dates. I had to pursue him, and even then, it felt like I had to talk him into why going out with me would be a good idea. If he did initiate a date, he consistently forgot his wallet. Every time. I let it go on longer than it should have because I was mega lonely and was still doing personal growth work in therapy but didn’t sufficiently value myself.

19. I dated a guy once who was extremely active on Reddit. Commented on a lot of things and would get into arguments with strangers just so he could be “right”. Was obsessed with his comments getting thousands of upvotes, as if proving his point further that he was correct. At first I was like whatever it’s just the internet, but looking back it was really signs of poor anger management and always needing things to go his way. There was little room for compromise.

20. The guy I was recently seeing did some things in bed without asking that really affected my physical (thanks plan b) and mental health. I excused it and never told him how upset I was. I kept thinking he’d check in and make sure I felt ok about it, but he did not. I told myself that we had “communication issues,” and that I didn’t want to push it, as I’d be fine in the long run. I was so wrapped up in the confusion and infatuation/NRE phase. My brain turned to mush around him.
    And it sucks, because 50% of me still wants to be with him, shifting my clearly weak boundaries to make him happy.
    I’m learning to make my values and boundaries more stable, and the person I have feelings for is what can change. Not the other way around.

21. From my last experience of two months, let’s see:

    – Called anyone or anything she didn’t like stupid
    – Invited me to her house on the 4th date, introduced me to her room mate, then spent an hour talking to her in her native language while I was ignored
    – Was rude/sarcastic to a waiter
    – I was making all the effort while she barely made an effort
    – Called the people of my home country “inbred” because according to her there are a big number of us that wear glasses
    – Global warming is not man made
    – I wanted to wait to have intercourse, but was happy to go down on her. Most of the time she got to orgasm twice, I never got to.
    – At a restaurant I told her I was full eating, but it was so good that I kept taking a bite or two every once in a while. She literally took my plate away from me.
    – Showed her my PSP that I bought in 2007, still working. Asked me if I was 12.
    – While discussing intercourse, I told her that its been a while since I bought condoms. She told me that its ok, there’s no need to use any because she takes her of herself.

    Should I continue?

22. Listen to how he talks about women

23. The problem with red flags is that everybody has them. We generally don’t know it’s a dealbreaker until we see a pattern. Otherwise we’ll knee-jerk react and dump everyone as soon as we see a flaw. In hindsight, the red flags seem obvious but that’s because by that point, we’ve seen the latter.

    For me, the red flags are if they aren’t respectful or if there is a behavior that prevents a relationship from lasting. An example of the latter for me was when he had a ton of female friends and then was making new ones after we were exclusive, but couldn’t handle the thought of me doing the same. I waited until there was a pattern to jump ship. I didn’t need to wait until he cheated, which I found out later he had a history of.

24. With women I’ve dated? In the last three years I’ve encountered too many of these to list. But to start…

    – Being cagey or outright lying about their personal history, family situation, or career. Instead of saying “it’s a little too soon for me to be comfortable discussing that” or something a normal, mature person would say.
    – Extremely sweet and supportive but snaps to rude, hostile and insulting/disrespectful when questioned or disagreed with.
    – Poor boundaries with male friends and acquaintances / courts romantic attention from these people while with you.
    – Overshares details about their sex life when they were with exes and hookups.
    – Uses issues in their personal life to make you feel had about asserting a boundary.
    – When discussing past relationships, portrays the ex as all bad, and themselves as all good, with no in-between.
    – Has a history of cheating but blames the cheated-on party for her behavior.
    – Insists that you take responsibility for her mental health issues.
    – Accuses you of having mental health issues of your own in response to you saying certain behavior makes you uncomfortable.
    – Lies about STI testing, refuses to show results, or lies about having an STI (dealt with all three of these scenarios in the last 3 years personally but came out unscathed).
    – Does inappropriate things like screaming, hitting, punching, or shoving and then says that you “caused” her to do it.
    – Portrays normal criticism or boundary-setting as “abuse” or “being controlling” and otherwise uses it to justify the item above.
    – Abusive to children or pets.
    – Mocks or makes fun of you in front of other people or to get attention.
    – Presents as single or otherwise hides you on social media.
    – Openly insults, mocks or belittles your appearance.
    – Insults, mocks or belittles your passions, interests, friends, or how you choose to spend your time.
    – Intrusive questions about income, career status or other “tells” of that nature.
    – Withholds affection if she has a problem with you or she is not getting her way in an argument.
    – Utilizes the silent treatment as a conflict resolution tactic.
    – Utilizes cursing and profanity as a conflict resolution tactic.
    – Triangulates people close to you in order to get her way in argument.
    – Lies or falsifies information about you to get her way in an argument.

    These are all things that have happened that I saw bits and pieces of and ended up being forgiving of until it was too late.

25. I hate to say this but: He didn’t felt any sexual attraction to you. He didn’t actually liked you.

    He friendzone you. He had a good time with you, but that’s all.

26. I am a walking red flag it appears.

27. Recent red flags I shouldn’t have ignored, but did:

    – still processing a breakup from a toxic ex
    – oddly competitive with me (later realized this was an attempt to assert dominance)
    – acting in love almost immediately, without having spent the time to really get to know me

28. He sounds like he has lost interest and doesn’t want to say it. Either he started dating someone else or he felt like it was dragging out.

    It’s like he started fading you instead of cutting it off and just progressively became snarkier.

    You don’t want to date someone like that, anyway. You’ll never know when they have a problem with you. If you’re confused now and they mock you when asking for clarity, you’ll be even more confused when you start dating them and they’ll still mock you to avoid being honest about what they want and need later.

    I get the need to put your best foot forward, but if you get a lot of mixed signals and asking about it doesn’t clear anything up, you’re getting a no.

    Things I look out for:

    * external locus of control (everything is done for/because someone else, people “make them” feel, say, or do things)
    * stonewalling
    * blows things out of proportion
    * expects me to do all of the work

29. him not telling me about his child until introducing me to him on the first date smh

    i had one guy after 3 days of talking get upset I was talking to other matches. I stopped talking to the other matches based on this guy saying all the right things. he canceled on me the day of our date and then got too busy for dating after lol.

    these two things made very clear boundaries for so it doesn’t happen again. I ideally am just looking to try and date people with the same end goals. But talking about kids and what the end goal for me looks like is probably a “red flag” to most men dating casually to find their long term partner