Has anyone dated someone like this?

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This topic contains 44 replies, has 1 voice, and was last updated by  Dangerouse 6 months, 1 week ago.

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  • #755261 Reply


    Hi I have just been on a second dinner date with a guy. i feel comfortable with him and like him and we have a good laugh over text and in person. He likes joking around though.but it’s getting hard to know when he is being serious or joking. I’m fun and joke as well but I’m more serious in nature I guess.

    So after each of our dates he follows up with a text chat an hour or so later and kind of asks me out again but not directly as a guy would say ‘I had a great time I would love to see you again etc.’ he is more if we did go there next time we could do etc so I will follow up with are you asking me out on another date? His reply will be well if you asked me I wouldn’t say no. So then I say I don’t ask men out and he turns it into a joke and says that’s a shame because I would definitely say yes !

    He takes this as he is asking me out but I don’t know it’s almost too passive for me. He will also not pick the venues etc tells me I did a great job last time etc. I’m not a decision maker and it’s hard for me to take the lead as it’s not natural for me.

    He turns up on time, is polite and fun but it’s like he is passive but very interested. He will initiate 95% of the time. I’m just not used to this passive and joking around and I’m not liking this aspect of him to be honest. I can tell he is nervous on our dates. He has said he has made a few friends in dating but that’s not what he is after and I can see why he would get friend zoned.

    Has anyone else had something like this? Is it lack of interest or ?

    #755263 Reply


    No, but I would say stop asking him if he is asking you out.

    If it bothers you so much break the cycle now. If he can’t properly ask you out then onto the next.

    It appears to me you don’t like a passive guy and dating is about finding the right match. He isn’t the only guy around so keep dating.

    #755265 Reply


    @Khadija thanks it’s just obvious that that’s what he is doing asking me out but its not direct and confident. He turns it all into playful banter🙄

    There is so much to like about him though and last date he kissed me and it was pretty great. At least I don’t feel like he is angling for bedroom dates.

    #755266 Reply


    @Khadija thanks it’s just obvious that that’s what he is doing asking me out but its not direct and confident. He turns it all into playful banter🙄

    There is so much to like about him though and last date he kissed me and it was pretty great. At least I don’t feel like he is angling for bedroom dates.

    #755274 Reply


    You don’t respond in a way that prompts him to ask you.

    If he says, next we should do x. You should respond and say, I’m free on x day(s) let me know if any of those days work for you.

    Don’t text back, are you asking for a date. I don’t know if it is his insecurity or awkwardness, but him probing to see if you are asking for the date sounds to me as if he is fishing to see where your level of interest is in him.

    So don’t go there. Just provide availability and leave it up to him to finalize a day and time. Regarding you having to pick the venue, it may be he wants to overly please you and thinks he can’t fail if he allows you to decide on where to go. Many women might suggest this is laziness, but in his case, I don’t think so. His joking all the time could be his way to mask social awkwardness and insecurity about dating.

    Up to you if you want to continue. The whole,point in dating is to meet someone you find compatible. If you aren’t sure after two dates you can try a few more, but if this feeling lingers, it would be best to just move on.

    #755276 Reply


    I think its just the initial newness and awkwardness whereas he probably doesn’t know how to go about it, was never taught, and just winging it in the only way he knows how.

    Back in the day men and ladies were taught to court because parents were active participants in the process but those days are long gone so the younger generation is just flailing about lol.

    I would stop trying to follow a ‘by the rules’ book with this one. Just know men like to play and if you learn how to play dating can be a lot of fun if you just go out and have some fun! Maybe try to learn how not be so serious :o)

    #755290 Reply


    He is a passive Beta make. Low confidence and self-esteem. He wants you to take the lead. Laziness and shaky self-esteem go hand in hand. This will color your entire relationship If you are ok with making all the decisions & doing all the work, then go for it. But the fact you are complaining about his passivity from the get go means you are not going to be happy with a passive guy. In fact this type of man wont tell you what his needs are or if hes unhappy about something. He will go with the flow to avoid conflict. Then when his resentments have built up too high, he will communicate in passive aggressive ways. Cheating may very well happen also.

    #755302 Reply


    I find it’s easy to find genuine intentions behind joking. In my experience the joking guy has not been serious, and often insecure, and hung up on an ex or worse yet in a relationship and cheating. Also a passive guy in my experience actually has their heart somewhere else and is out to get an ego boost. I would tread carefully. Sorry to be a downer.

    #755303 Reply


    Could it be that this passive fellow is just not much interested in women but feels that he ought to be?

    #755305 Reply


    Im not sure if he is that passive. You both sound insecure though. Him about asking directly for a date and you avoiding in letting him know you are interested. A good friend (funny, interesting and good looking) of mine was very clumsy and shy about dating. He also showed up on dates too late. The woman decided she had to make the move and pretty much literally dragged him into bed. They now have two kids. I think looking background was still hung up on a girl he dated when he was twenty because she was mentioned when he turned 50 and we, old high school friends were like, what? That was a two month fling.
    Anyway im sure she is wearing the pants in that relationship but the upside is he is a great father and will probably never cheat seeing how clumsy he is lol.
    So if you like this guy, try to be direct and do what omg suggested, just point out a few dates that you are available. It has just been two dates anyway so its way to early to tell what his normal behaviour is

    #755549 Reply


    We are both mid 40s and his children are younger than mine. He has 50/50 my ex husband has 9% so only one night a week.

    It’s school holidays and he has taken his children away for a week holiday and because we have talked about the next date but no day and he joked that I should ask I calculated that by his arrangements that he could be free not this Saturday but the next so I asked him if he was free. His response was a serious not joking one that he can’t tell me at the moment because his ex wife is also away and won’t be back but a grandparent is going to help but the dates are not sorted.

    I sent a message back that it was ok and let me know. But I just get a gut feeling that it’s low interest not because he said he can’t tell me but just a feeling. He texts me randomly during the day every day or so to say random things so sharing a thing out his son or a funny work thing and then there is the after dinner back and forth chats that will go on until bed time (Not sexual at all) but there seems to be not enough wanting to make a date or am I rushing it?

    I just feel like getting to know someone slowly is fine but I’m not getting the when can I see you next but after each date an enquire as to can we see each other again if that makes sense?

    I have had other men that I have talked to on the dating site ask to meet me but I’m not keen to go on dates with other people if I’m interested in someone. So I guess this is why I wanted to ask him. I would like to get to know him more but texting over meeting isn’t what I’m after. We have chatted over text way more than in person. Both are great but I’m not sure if I’m wasting time just dating him and waiting for him to be free to see me.

    #755559 Reply


    Lonnie – you are spot on. OP listen to Lonnie’s advice.

    #755563 Reply


    I haven’t experienced this before and I was thinking that maybe @Lonniewas being all doom and gloom but I guess this maybe isn’t for me.

    I’m used to guys online fast-tracking to try and bed you so this slow pace I wasn’t sure about.

    It’s a shame because I enjoy his company. I think will just sit back a little and see what happens.

    I almost don’t expect to hear from him until he returns from his holiday. His focus is on his children as it should be. I sent a text to say enjoy your holiday. There was no response back. But I would have said ‘thanks!’But by putting it like that I guess reads as I’ll talk to you when you get back.

    Texting = one way to send yourself mental with etiquette.

    #755576 Reply

    Liz Lemon

    The fact that he’s not setting a date/time to see you again says it all. Texting you daily doesn’t mean much, he may like you well enough and find it entertaining to text you, but what good is texting if he won’t lock in a date to see you again. The nightly texting may actually be working against you because if he can chat with you over text every night until bedtime, that may be enough for him emotionally/mentally at this point, so what motivation does he have to see you again anytime soon?

    To clarify– you are only without your children & free to date 1 night a week? And he has 50% custody of his kids? It sounds like the custody schedules will make it difficult for you two to connect.

    If i were you I would most definitely be going on dates with other guys from the dating app. You could be missing out on opportunities with other guys who are just as nice as this one who are actually willing to meet up with you. You’ve only had 2 dates with this guy and he’s demonstrated that he’s in no hurry to see you again. If he gets his act together and sets a date and time to see you again, great, but in the meantime don’t wait around for him.

    #755579 Reply


    @lizlemon yes you are correct I only have one night a week and but Im free from 8am sat – 6.30 Sunday so all weekend,
    He does the usual every second weekend fri-sun and two days a week.

    I guess he follows up a date within an hour and tells me he wants to see me again. Last date he worked from home so we could at least have lunch his suggestion but I knew he was going away this week and I was away last weekend before that when he was free when he thought we had a date booked in.

    I can date during the daytimes as I’m self employed and flexible with my time.

    We only met a few weeks ago so I don’t want to jump ahead of myself and make snap judgments. but he did think we had a date last weekend and only realised he thought this when he suggested restaurants for Saturday night.

    We also don’t text chat every night just maybe twice a week. But I do feel like I’m loosing a bit of interest. I would like an evening date with wine to maybe see what the vibe is. two daytime dates feels a bit harder to feel relaxed.

    #755637 Reply


    Wait – You are after the second date and You start analyzing deeply personality of this guy?
    I guess I know better my shop assistant at my favorite shop.
    For sure – You almost know nothing about him, so make a favor for Yourself and him – just give time for this relationship to grows/appears. Just have fun together and see how it can work without additional distractions from Your imagination :)

    #755960 Reply


    I thought about staring a new thread but thought it would make more sense to continue. I’m not sure what to do here at all. I do like this guy a lot but I’m being cautious. There are things that have made me question things

    I was surprised that he contacted me while away on holidays with his children and friends. He contacted me and I sent back a quick reply as he is with family, he then pushed for more of a chat so I did so on two of the occasions. I sent a message yesterday morning. I thought seeing as he seems to like things balanced between people I would initiate a text just to say hey, i added an inside joke and left it at that. But it didn’t require a reply but there was nothing he didn’t even laugh at it or indicate that he has seen it. He has done this a couple of times when I initiate he will not really reply but when he initiates which is 90% of the time he will text to get a conversation going. Like he will send a message and wait a few mins and send another. I totally get that he is busy with family and I didn’t expect for him to text at all when he is away. When I have said I have to go he has said text me back later if you feel like it which last time we spoke I didn’t as I went to bed.

    But not responding to my initiated text again for 36 hours and counting just feels a bit odd. I always respond to his texts even if its a few hours later if I’m out.

    The other thing was he got into a chat with me on his second night away. I’m this chat he said he is feeling a bit nervous taking to me. I laughed and said why and he said he is thinking about us kissing again. But this time he wants me not to run off afterwards. He then asked if I would make the first move this time, he was joking around saying will you kiss me back if I kiss you ? It was a bit of an odd conversation and I got a bit worried he was going to get into a sexting kind of thing just with words but he didn’t ( I wouldn’t have gone there and he would have lost me if he did) but it felt a bit odd. Maybe I could almost say I felt a bit toyed with? It was like a playful conversation but felt like we were 14?

    I have noticed that he isn’t active on tinder since we have stated taking unless he only swipes at home. I am still active and are just taking to other men. I only do this at home though.

    I don’t know something is starting to trouble me a little and it’s not the fact that we had a date a week ago and we don’t have another date set even though he has asked me to see him again.

    Any thoughts? I’m not sure if I should back away a bit or I’m being weird about normal things. He seems like a nice guy so far. One thing he did say was he just wants to get to know me without checking the usual yes no boxes he said it’s not that he isn’t interested in me because he is but he doesn’t feel like he has to find out exact things about me like length of time I have been divorced and wants to just let it unfold in a more organic way as he is over the interview like nature of online dating.

    Sorry I’m just not sure if I should continue?

    #755966 Reply

    Better off single

    The red flags you see now are going to be the reason you break up later.

    #755967 Reply

    Better off single

    Or even the small things that bother you that arent red flags. You will be so annoyed by them later you will want to break up or wish you were somewhere else.

    #755980 Reply

    Liz Lemon

    You’ve barely started dating this guy. You’ve had what, 2-3 dates? And you’re already agonizing over so many things. Look back at what you wrote.

    I don’t think you two are a good match. You shouldn’t be this anxious over a guy you barely know that you’ve only gone out with a few times.

    Also, I question this: “he doesn’t feel like he has to find out exact things about me like length of time I have been divorced and wants to just let it unfold in a more organic way as he is over the interview like nature of online dating”. There are some things that you have to know about a person you’re dating. I understand being tired of the interview-like nature of dating, but dating is essentially interviewing a potential partner. You have to get exact information and screen people. Knowing the length of time someone has been divorced is extremely important when dating– there’s a massive difference between dating someone who is divorced a few months versus divorced a few years. A potential partner has the right to know that. So it’s strange to me that he doesn’t want to know the basics about you.

    #755990 Reply


    Totally crazy OP. Two dates and all these questions. You do what almost every woman does wrong. You have a date or two and then start planning a future with the guy. Completely nuts.

    #756018 Reply


    @ Lizlemon

    “he doesn’t feel like he has to find out exact things about me like length of time I have been divorced and wants to just let it unfold in a more organic way as he is over the interview like nature of online dating”.

    No he said this to me!

    #756020 Reply



    “he doesn’t feel like he has to find out exact things about me like length of time I have been divorced and wants to just let it unfold in a more organic way as he is over the interview like nature of online dating”.

    No he said this to me!

    #756021 Reply


    I guess I’m not ready for dating. I’m still worried if I will be pulled into a bad relationship and not certain if I will see clearly the signs.

    #756025 Reply


    No. You sound totally nuts.

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