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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:
shuggles · 24/08/2025 15:44

Mmhmmn · 24/08/2025 10:32

Agree - generally men are the desperate ones cos they’re shit at being on their own and need a carer partner.
But society tells everyone nonsense and lies to keep up the pitiful spinster impression of single women.

Well that's a bit rude. I would have thought that men are no different than women when it comes to being single. Many single people would like to have a partner, but the idea that women specifically are desperate to find a partner urgently to have children is that part that's rooted in fantasy.

Returnofjude · 24/08/2025 15:28

Muffsies · 24/08/2025 13:25

It's a huge generalisation, but I have seen evidence. Women who are happily on their own are seen as scary nutcases, or sad and unattractive. Men on their own are seen as hapless and coping badly, desperate for attention and female help to sort their lives out. In both cases it's seen as a abnormal and looked down on, like we're pathetic if we're not with someone.

I suspect if more of us learnt to be happily on our own we'd be better people, and not be so keen to push ourselves or others into expected roles. It's annoying that society shoves us into coupling-up as soon as possible as the desirable thing.

What “evidence” have you seen?

I am a woman.
I have been single post divorce for 6 years
I am very happy and fulfilled and never even got a whiff of feeling judged

My ex
is a man (with whom I remain close friends with)
Also been single for 6 years post divorce
Also very happy and not remotely regarded as a sad case by any of my friends, our mutual friends or indeed I suspect his own friends.

Muffsies · 24/08/2025 13:25

Mmhmmn · 24/08/2025 10:32

Agree - generally men are the desperate ones cos they’re shit at being on their own and need a carer partner.
But society tells everyone nonsense and lies to keep up the pitiful spinster impression of single women.

It's a huge generalisation, but I have seen evidence. Women who are happily on their own are seen as scary nutcases, or sad and unattractive. Men on their own are seen as hapless and coping badly, desperate for attention and female help to sort their lives out. In both cases it's seen as a abnormal and looked down on, like we're pathetic if we're not with someone.

I suspect if more of us learnt to be happily on our own we'd be better people, and not be so keen to push ourselves or others into expected roles. It's annoying that society shoves us into coupling-up as soon as possible as the desirable thing.

ConfusedChristina · 24/08/2025 10:36

Hello, l think the over 95% of the poll gives you the answer.

He has red flag written all over him. Sometimes it is better to call it a day and move on.

l know it’s not easy and dating is hard, however the next guy is looking for you, so get back out there and find him.

Take care of you

Mmhmmn · 24/08/2025 10:32

shuggles · 21/08/2025 23:54

@JMaggs93 He's obsessed with the idea that all women are clingy and desperate. This is a popular view among certain men because they like to think that women receive their comeuppance in later life, and they revel in the schadenfreude.

Of course, people who live in the real world know that the desperate 30-something woman is a stupid media stereotype that does not exist in reality.

Agree - generally men are the desperate ones cos they’re shit at being on their own and need a carer partner.
But society tells everyone nonsense and lies to keep up the pitiful spinster impression of single women.

ZenGarden89 · 24/08/2025 09:37

The ick should always be listened to. I’d absolutely love to know the reason for his bad co-parenting relationship.

Negging is so vile and insidious and points towards a deep rooted misogyny where overtime a person is left feeling confused, diminished and essentially being gaslighted.

The fact that he couldn’t help himself on only your third date suggests it’s one of his favourite pastimes and I’m glad for you that you’ll be able to make a swift exit. Rather than ghost or peter out I’d email him and just say you don’t think you’re a good match. If he replies don’t bother responding. Don’t let this put you off dating, you just came across an abuser and thankfully he has shown his colours early.

Unexpectedlysinglemum · 24/08/2025 00:23

I think he watches lots of manosphere red pill nonsense. Would love to hear the exes side of the story!

FattyMallow · 24/08/2025 00:11

It's good you didn't respond him immediately. The problem with such men is that they're good at evaluating others but not themselves. You can't build any relationship with a person that sees children as a burdain, let alone analyse his mistakes to solve a relationship hardship, that all couples go through. Honestly, he isn't worth even a one night stand.

As for sacrifices they should be equal on both sides.

GreenFingeredClara · 23/08/2025 17:39

He gives you the ick. Reason enough to call it off. There are plenty of other men out there and you can take your time meeting a few more and deciding whether any of them are good enough.

Some years out of a long marriage, I am not willing to settle, and don't feel I need to. I've been dating to put myself in the way of opportunity, and because meeting people, hearing their stories, trying new restaurants etc is better than another night in front of the telly.

You may decide (as I seem to have, at least for the time being) that you are better off single, enjoying occasional dates as an evening out and seeing if you feel like meeting again, rather than thinking about each one 'is this my next partner?' I used to be very much half of a couple, now I am a whole, independent person in my own right. I'll share if I find someone I want to share with, but not if he gives me the ick!

vegetarianlouise · 23/08/2025 16:52

JournalistEmily · 23/08/2025 16:36

Ick central. But tell him why!

This.

JournalistEmily · 23/08/2025 16:36

Ick central. But tell him why!

Starrynight73 · 23/08/2025 11:37

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.

This guy is giving "im the prize" vibes and testing your responses. Clearly he has expectations around what he feels he is looking for long term. You can either speak to him about how this has made you feel...really pay attention to his response, defensive or validating? Or duck out now and save yourself weeks, months of investing into someone who is not for you

Marelli · 23/08/2025 11:16

One word for him
"NARCISSIST"
Weird red flag questions & comments, that give quite an insight to his personality & what he thinks of himself & others.

Time for curtains on that one.

A heads up..
There is a chance his ego won't like being rejected. If I'm right you've had maybe just four dates? thankfully it's early on, so a better chance he could disappear but there's so much more than just the meetings, there's the chatting, messaging etc that all goes to form those bonds & feelings, so I'm going to say depending on where this relationship is emotionally, do be mentally prepared for if he responds negatively, could be name calling & belittling or a little manipulation to try & get you to stay with him, some of that love bombing.
If you do end things, be sure you make it clear & to the point, don't give any room for misinterpretation & then do not respond to him again, whatever he responds with.

G5000 · 23/08/2025 11:06

Newname42 · 23/08/2025 07:56

i think it was about the pregnancy, karate is a martial arts contact sport which you have to stop during pregnancy for safety reasons, not the time after the baby was born

He asked if she would give up karate. Women pause many activities during pregnancy, that's different. It's like asking if she has ever considered giving up wine, unpasteurised cheese and handling cat litter - surely an odd way to put it, if you just mean during pregnancy.

NotPerfectlyAdverage · 23/08/2025 11:05

It's hard when your on the spot, but in the ideal world when your processing speed is on fire you would ask him

"Do you see your child as baggage and wonder what I saw in your profile?

Then be a politician and not answer his question.

Just reply with "what an insightful question" that confusses most with a insult being taken as a complement

Returnofjude · 23/08/2025 11:00

vegetarianlouise · 23/08/2025 10:58

I would like him to tell me in his own words "what he thinks of single mothers like me", I want to hear it, details and all.

It's going to be a fun blood fest 😈

Edited

Yes

but you’d also advise your DD the same, and that is what I find odd

vegetarianlouise · 23/08/2025 10:58

Returnofjude · 23/08/2025 10:37

You may like to take the risk

but to advise the same if your single mother daughter would be reckless

andyou didn’t say that originally

you suggested to give him benefit of doubt and go on another date with him!!

Edited

I would like him to tell me in his own words "what he thinks of single mothers like me", I want to hear it, details and all.

It's going to be a fun blood fest 😈

Lovehascomeandgone · 23/08/2025 10:44

Sparklesandspandexgallore · 23/08/2025 07:45

This might sound awful but someone who has had a failed relationship and a child by the age of 27 is in no position to be that choosey.
I have no idea what the karate comment was about. Did he mean it’s a physical sport so you might not want to do it whilst pregnant? Strange question.
Regarding the baggage- he is the one with more of an issue. Most men that age haven’t ended up in his postion.

@Sparklesandspandexgallore you are fucking kidding me right? I hope you aren’t female but if you are, check your attitude. She has every right to be choosy and having a child does not put anyone at the bottom of the barrel.

Returnofjude · 23/08/2025 10:37

vegetarianlouise · 23/08/2025 10:18

I've usually dated good folks and lack any sort of drama in the relationship department. I don't have a daughter either but if i had one I would advice her this man has red flags all over and to ask him "what he meant exactly".

I just love to call the BS on people, it's a hobby of mine.

You may like to take the risk

but to advise the same if your single mother daughter would be reckless

andyou didn’t say that originally

you suggested to give him benefit of doubt and go on another date with him!!

ozzycat95 · 23/08/2025 10:33

No, not being unreasonable at all. He sounds like an egotistical, nasty piece of work and potentially controlling with the comment about giving up karate.
A guy I went on a date with a couple of years ago told me I was ‘beyond the usual age for settling down and having kids’ (I was 27) and asked me if I thought it would be possible for me to have a long term relationship in the future seeing as I’d ‘only’ had one long relationship before. He also said horrible things about his ex. Needless to say I didn’t see him again.

I would tell this guy you’re not compatible and block him. You don’t owe him anything after three dates.

JMSA · 23/08/2025 10:27

Splash! The sound of you throwing him back in the sea 😅

DadBodAlready · 23/08/2025 10:24

Men are from Mars, Women are from Venus.

It may be that he's really interested in you and trying to get a handle on your views. His comment about your baggage, he could be trying to understand whether you see this as a bit of fun (especially) as he's younger or whether you are see this as a potential serious relationship. His comments about your karate, maybe he's trying to determine whether you are open to kids in the future.

He may be getting way ahead of himself as its only your 3rd date, and really clunky in his approach, but next time he asks what you think is a weird question just ask him 'why do you ask?'.

Then again I could be completely wrong and he's a total weirdo

vegetarianlouise · 23/08/2025 10:18

Returnofjude · 23/08/2025 10:12

So the answer is… yes, you would encourage your DD to give this man the benefit of the doubt and go on another date with him.

What is your relationship history like for you to remotely think this would be sensible and in the best interests of your daughter and her children?

I've usually dated good folks and lack any sort of drama in the relationship department. I don't have a daughter either but if i had one I would advice her this man has red flags all over and to ask him "what he meant exactly".

I just love to call the BS on people, it's a hobby of mine.

MellersSmellers · 23/08/2025 10:14

If you can be bothered...challenge him why he said that given he has the same "baggage".
Stand proud, and if you're not feeling it move on.

Returnofjude · 23/08/2025 10:12

vegetarianlouise · 23/08/2025 10:10

I would like my DD to be smart and inquisitive enough to corner this man and ask him exactly "what he meant" so she can call the BS on him (if needed) then walk out of this relationship confident enough knowing that she dodged a massive bullet. Maybe it's the fact English is not my mother language and his words regarding her "baggage" were a bit "confusing" to me but not to you (and that's ok).

So the answer is… yes, you would encourage your DD to give this man the benefit of the doubt and go on another date with him.

What is your relationship history like for you to remotely think this would be sensible and in the best interests of your daughter and her children?