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Date asking strange questions

311 replies

JMaggs93 · 21/08/2025 15:22

Wanted other's perspectives on this as I've been out of the dating game for a while and have been taken aback by questions this man has been asking me on dates.

I'm 32 and he is 27. We met online and spoke for a while, then decided to meet up. Our first couple of dates were lovely and he seemed really nice and genuine. On our third date we went to watch a film where the leading lady was going on a date herself, a single parent etc, much like myself.

I was driving so on the way to drop him home afterwards we were chatting in the car, and he suddenly asked me if karate (I've been doing this for a few years and love it) is something I'd ever think about giving up in future. I told him of course not, why would I? He then said maybe I'd have to if I wanted anymore children etc which honestly right now I don't want for personal reasons. I found this an odd thing to say but let it go.
We were talking about the movie and the female character who was getting back into dating. He then asked me if I ever wondered what he saw in me on the dating app we met on. More specifically, did I ever wonder what he saw in me and 'all my baggage'? Obviously he meant my kids and my bad experiences with relationships which I'd told him about briefly whilst we were first chatting.

I immediately caught the ick. I was so shocked I didn't really give an answer but it's made me think that he believes I should count myself lucky that a younger man chose me despite my 'baggage'. For context, this man has a child of his own and a bad co parenting relationship with his ex, so really if he thinks what I have is baggage then surely he has the same?

I guess what I'm asking is, am I being unreasonable for feeling really put off and belittled? Like I'm not quite good enough but he picked me anyway? I did like him a lot but after this I feel really weird about him. He's been messaging me as normal and wants another date but I've been giving him short answers and avoiding for the most part. I feel really deflated after plucking up the courage to get back out there.

OP posts:
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TFImBackIn · 07/03/2026 16:23

Well he revealed his true self pretty quickly, didn't he!

valentinka31 · 31/08/2025 10:38

BeenzManeenz · 30/08/2025 14:42

27 is by far and away an adult (I say this as someone in my 40s) and saying borderline abusive stuff it not tripping up over your words.

Incredibly insulting to people on the spectrum by the way. Being neurodivergent is not a synonym for being a twat!

Yes 27 is totally an adult, and has been for some years .

But as for neurodivergent - well, it's not being a twat, because it's not fully intentional/cognisant of the effect, but I do have a friend who is very ndv and he says things that make me reel and then I have to just put it in the context of him - if anyone else said what he says, I'd never speak to them again. But he doesn't mean it like that.

BeenzManeenz · 30/08/2025 14:42

lotsofpatience · 29/08/2025 03:11

He's 27 and tripping himself up by not filtering what comes out his mouth. Cut the guy some slack. He may be in the spectrum

27 is by far and away an adult (I say this as someone in my 40s) and saying borderline abusive stuff it not tripping up over your words.

Incredibly insulting to people on the spectrum by the way. Being neurodivergent is not a synonym for being a twat!

LadyjaneOnSteroids · 29/08/2025 18:38

Are you psychoanalysis your date or assuming things without actually asking him 'what do you mean by that?' Or 'I'm not sure where you are going with this.' Jumping to conclusions or assumptions can destroy what could become a beautiful relationship.

Previous bad experiences cloud our perspectives. We are more defensive and judgemental. Never again will we be betrayed, lied to, used; nor will we blindly trust. Others will have to EARN my respect and trust by running a psychological gauntlet by responding correctly to all my seeminingly innoccuous questions. I know, bc I I was devastated by a breakup and, yes, became very discerning and mentally aware.

I dont think his questions were unreasonable. I like open honesty rather than ppl who hold back their truths and emotions. To me, that's subversiveness and dishonesty. Don't pause before responses bc that means you are editing your response or lying.

If he asked if you would consider stopping your karate for childbearing, you can't assume he meant forever. He just wants children of his own. This is a normal desire for most ppl. You could suspend Karate for prenatal safety and do yoga. Martial arts keeps us healthy and it's beneficial to have those skills for protection for your family, kids and friends.

How do you know what a person is thinking when they ask a question? You don't, unless you ask. He may have been trying to find out what you thought of him and his baggage but thought it better to put the focus on you instead of coming across as self-absorbed if phrasing the question differently. We can't assume we know what he meant or why he asked, unless you ask for clarification.

If you feel uncomfortable, say so. If you feel insulted, tell him. Why let something fester or turn you off when it could just be word choices or misunderstandings. Men don't express themselves as well as women, bc they dont sit in a group of guys talking abt feelings, psychology or situational crises like women do.

We don't need to make anyone jump through hoops or prove they aren't like past significant others who let us down. Give him a chance to speak and explain himself. Don't just get offended and cut him off bc he touched a sensitive spot or said something 'wrong' that triggered your Spidey Sense.

Some day, you could be with someone you are really attracted to but they suddenly, without warning, give you the cold shoulder and stop speaking to you. Dump. That is hurtful, unkind and unnecessary. Even if your relationship doesn't seem like it will work, tell him so, tell him positive things but also tell him why you aren't ready for more [with him]; though you dont want to hold him back. Ask to remain just friends...don't make him feel rejected or a failure. Dating new ppl is stressful enough.

Take off the Prickly Pear jacket and give him a chance to explain himself. Even if it's just a phonecall. It sounds as if attraction is there.

lotsofpatience · 29/08/2025 03:11

He's 27 and tripping himself up by not filtering what comes out his mouth. Cut the guy some slack. He may be in the spectrum

CATomas · 29/08/2025 01:21

My guess is that women who habitually choose rotten men have issues that probably go back to childhood.

HardyCrow · 28/08/2025 21:45

BySassyGreenPanda · 28/08/2025 15:09

I had a friend who did this. Opened the floodgates straight away every time.

Of course she met another awful man. One time she had the guts to call him out on something.

He said she'd accepted much more abuse in the past, so had no right to challenge him over this. That he should be able to be at least as abusive as her ExH was before she even said anything..... What a prince.

She was so broken. A shell of a human because of these men she insisted on staying with.

Some men are so shit

TalulaHalulah · 28/08/2025 18:11

BySassyGreenPanda · 28/08/2025 17:25

I haven't read any threads encouraging them to date abusive men.

Vile people can and will weaponise your story. I've been there. So kind, loving and empathic - until he wasn't...

If you think I'm victim blaming then so be it. I don't give a shit. This is the world we live in. No, we shouldn't need to worry about this but we do have to.

Showing vulnerabilities attracts potential abusers. End of.

I agree with you.
I also agree that women need to know this.
But it was not your fault for sharing your story, it was not my fault and it was not your friend’s fault. That’s all I mean.

The threads I was talking about judge single mothers for the choices they made first time around or that ended up with them being single mothers. No, they are not encouraging them to date abusive men (but as you say, abusive men don’t come with signs on their heads). But they are suggesting single mothers have done something wrong, which does then lead to a defensive position of thinking you need to explain how you became a single mother. It’s all very well saying well, you don’t need to explain because it attracts predators but how do you know that? You know that because you explained. Been there, done that as well.

So my starting point is saying, let’s not blame the women who explain because they feel the need to (and they think they are telling an empathetic man); yours is saying well, women don’t need to explain because it attracts predators (who can be charming, empathetic men). Both points can be true.

(edited to add: I am not sure my posts deserve an eye-roll, though 🤷🏻‍♀️)

BySassyGreenPanda · 28/08/2025 17:25

TalulaHalulah · 28/08/2025 16:53

SassyGreenPanda I don’t think you have read any of the recent threads judging single mothers, but that apart, it would have been possible to make all the points you make in your most recent post without victim-blaming your friend. Have her corner, don’t judge her.
And domestic abuse and coercive control is gendered precisely because of wider patterns of social conditioning. But I don’t think this is anything radical to say.
And if single women were of high value to single men, then men would not be abusing said women.

Edited

I haven't read any threads encouraging them to date abusive men.

Vile people can and will weaponise your story. I've been there. So kind, loving and empathic - until he wasn't...

If you think I'm victim blaming then so be it. I don't give a shit. This is the world we live in. No, we shouldn't need to worry about this but we do have to.

Showing vulnerabilities attracts potential abusers. End of.

moomoo1967 · 28/08/2025 17:05

Oh my word that is vile, but precisely why it's wise not to divulge every detail of your past. We all have all felt that we should be honest with new relationships but the past is the past and should stay there IMO

BySassyGreenPanda · 28/08/2025 16:58

moomoo1967 · 28/08/2025 16:42

Oh my word that is vile, but precisely why it's wise not to divulge every detail of your past. We all have all felt that we should be honest with new relationships but the past is the past and should stay there IMO

I know but apparently that view is victim blaming. 🙄

No one should be looking to exploit vulnerabilities but some are. You can't love an abuser into becoming a decent bloke. If you end up with one he will never change but you will.....

You need to prevent these people from getting into your life. If you're projecting something they're looking for, you'll attract them. So, stop doing it.

TalulaHalulah · 28/08/2025 16:53

SassyGreenPanda I don’t think you have read any of the recent threads judging single mothers, but that apart, it would have been possible to make all the points you make in your most recent post without victim-blaming your friend. Have her corner, don’t judge her.
And domestic abuse and coercive control is gendered precisely because of wider patterns of social conditioning. But I don’t think this is anything radical to say.
And if single women were of high value to single men, then men would not be abusing said women.

BySassyGreenPanda · 28/08/2025 16:48

TalulaHalulah · 28/08/2025 16:02

Let’s be clear that the blame here lies with the man for behaving appallingly. And possibly also with social attitudes for judging women when they are single, especially if they have DC, and making they feel like they owe people an explanation for this. Or are worth less because of this.

A decent man would have made sure to treat your friend right, not seen his opportunity to carry right on where her ex left off.

Let's be even clearer.

*Judging women when they are single, especially if they have DC
No one is telling women to date awful men just so they aren't on the shelf. Especially if they have children. Check the treads on here.

*Making they feel like they owe people an explanation for this
No explanation needed. The only response required when asked why you're single ''at your age' is to say 'because my last relationship ended'. That shuts that shit down straight away.

*Or are worth less because of this
Then we need to work on not giving a shit about what people think. Single women are of high value at any age. Just ask single men.

EDIT: Typo

moomoo1967 · 28/08/2025 16:42

BySassyGreenPanda · 28/08/2025 15:09

I had a friend who did this. Opened the floodgates straight away every time.

Of course she met another awful man. One time she had the guts to call him out on something.

He said she'd accepted much more abuse in the past, so had no right to challenge him over this. That he should be able to be at least as abusive as her ExH was before she even said anything..... What a prince.

She was so broken. A shell of a human because of these men she insisted on staying with.

Oh my word that is vile, but precisely why it's wise not to divulge every detail of your past. We all have all felt that we should be honest with new relationships but the past is the past and should stay there IMO

TalulaHalulah · 28/08/2025 16:02

BySassyGreenPanda · 28/08/2025 15:09

I had a friend who did this. Opened the floodgates straight away every time.

Of course she met another awful man. One time she had the guts to call him out on something.

He said she'd accepted much more abuse in the past, so had no right to challenge him over this. That he should be able to be at least as abusive as her ExH was before she even said anything..... What a prince.

She was so broken. A shell of a human because of these men she insisted on staying with.

Let’s be clear that the blame here lies with the man for behaving appallingly. And possibly also with social attitudes for judging women when they are single, especially if they have DC, and making they feel like they owe people an explanation for this. Or are worth less because of this.

A decent man would have made sure to treat your friend right, not seen his opportunity to carry right on where her ex left off.

BySassyGreenPanda · 28/08/2025 15:09

moomoo1967 · 27/08/2025 10:44

One thing I've learnt when dating is to NEVER tell a date if you've been in bad relationships. It sets the precedence to them that, that is the way you expect to be treated

I had a friend who did this. Opened the floodgates straight away every time.

Of course she met another awful man. One time she had the guts to call him out on something.

He said she'd accepted much more abuse in the past, so had no right to challenge him over this. That he should be able to be at least as abusive as her ExH was before she even said anything..... What a prince.

She was so broken. A shell of a human because of these men she insisted on staying with.

ForNoisyCat · 27/08/2025 20:49

moomoo1967 · 27/08/2025 10:44

One thing I've learnt when dating is to NEVER tell a date if you've been in bad relationships. It sets the precedence to them that, that is the way you expect to be treated

I so agree with this!! I've only dated once since divorce, but I was careful not to let on too much of the dreadful stuff for that very same reason.

moomoo1967 · 27/08/2025 10:44

JMaggs93 · 21/08/2025 15:22

Wanted other's perspectives on this as I've been out of the dating game for a while and have been taken aback by questions this man has been asking me on dates.

I'm 32 and he is 27. We met online and spoke for a while, then decided to meet up. Our first couple of dates were lovely and he seemed really nice and genuine. On our third date we went to watch a film where the leading lady was going on a date herself, a single parent etc, much like myself.

I was driving so on the way to drop him home afterwards we were chatting in the car, and he suddenly asked me if karate (I've been doing this for a few years and love it) is something I'd ever think about giving up in future. I told him of course not, why would I? He then said maybe I'd have to if I wanted anymore children etc which honestly right now I don't want for personal reasons. I found this an odd thing to say but let it go.
We were talking about the movie and the female character who was getting back into dating. He then asked me if I ever wondered what he saw in me on the dating app we met on. More specifically, did I ever wonder what he saw in me and 'all my baggage'? Obviously he meant my kids and my bad experiences with relationships which I'd told him about briefly whilst we were first chatting.

I immediately caught the ick. I was so shocked I didn't really give an answer but it's made me think that he believes I should count myself lucky that a younger man chose me despite my 'baggage'. For context, this man has a child of his own and a bad co parenting relationship with his ex, so really if he thinks what I have is baggage then surely he has the same?

I guess what I'm asking is, am I being unreasonable for feeling really put off and belittled? Like I'm not quite good enough but he picked me anyway? I did like him a lot but after this I feel really weird about him. He's been messaging me as normal and wants another date but I've been giving him short answers and avoiding for the most part. I feel really deflated after plucking up the courage to get back out there.

One thing I've learnt when dating is to NEVER tell a date if you've been in bad relationships. It sets the precedence to them that, that is the way you expect to be treated

Wooky073 · 26/08/2025 23:16

Congratulations on exiting the 'relationship' and dodging that bullet :) Im sure there are good ones out there but they can be tricky to find. New 'relationships' are always exciting but before too long the mask does slip and they show you who they really are. It is good when this happens and we have to take notice of it. Enjoy a little more time for yourself before getting back on the horse so to speak :)

LadeOde · 26/08/2025 22:39

Anyway, too many red flags with this new fella and I'm glad the majority agree with me, again thank you all, he's long gone now!

@OP, Praise the Lord! Wish him safe journey.

Iamnotalemming · 26/08/2025 20:51

Well done @JMaggs93
Sounds like you dodged a bullet

Lavender14 · 26/08/2025 19:13

Sounds like there's a reason why he has a bad co parenting relationship and its him.

JMaggs93 · 26/08/2025 19:11

EDIT:

Sorry, I thought I'd just try to answer a few questions about the ex and the co parenting etc.
So he explained to me that when his ex became pregnant, they argued a lot and eventually separated and at first she didn't allow him to go to scans, be at the birth etc (I do not judge his ex at all as he didn't say why or what they argued about, who was in the wrong, but he did paint himself a victim.) She did then allow contact but was becoming flakey, for example, denying him access for this reason or that, he was always quite vague and I did have my suspicions that he wasn't quite pulling his finger out but gave him the benefit of the doubt.
On top of all this, it always went through my mind that if we ever became serious and he was having issues with his child and his ex, then that would be brought home to me and my own child which I did not want as my child enjoys our home and his peace now after the volatile relationship I had with his father.

Anyway, too many red flags with this new fella and I'm glad the majority agree with me, again thank you all, he's long gone now!

OP posts:
JMaggs93 · 26/08/2025 19:04

Thanks everyone, overwhelmed with the responses!
I appreciate everyone's opinions here and I do have some issues with self confidence and putting myself down due to past experiences. I should be quicker off the mark to defend myself and raise my standards, I'm getting there slowly!
I've since ended this relationship if you can even call it that with a handful of dates. He was very disappointed and when I brought up my concerns (ones I've mentioned in original post) he was a little defensive and tried to tell me 'that's just the way he is'. He said he'd have loved to pursue something with me but I told him I wasn't feeling it anymore, have a nice life blah blah blah.
Thank you again, all. Much appreciated 🙏

OP posts:
Realjournal123 · 26/08/2025 11:10

Trust your instincts. If you’re having these feelings now after such a short time, imagine what else will come out. Dont give it any more of your time. As the saying goes ‘ why give it 5 hours if you wont give it 5 years!