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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:
HonestOpalHelper · 22/08/2025 08:23

Sounds like a total tool, best to get away now whilst its easy to do.

PinkZebraStripes · 22/08/2025 08:17

No do not give him the benefit of the doubt! Honestly women.

He is playing you. He's keeping his options open for some mythical idea of perfection. Let him and his fragile ego go.

He's also quite fucking rude IMHO. He's marking out the territory of you being the fun thing on this side and not the main event. Fuck him off. As it also won't do your confidence any favours- do you want to start thinking like this person? As that's what will happen.

I have seen this many times in younger men. It's all good and well as long as you play into the narrative that they are doing you a favour. They cannot deal with rejection from an older woman. You have to ego stroke them, its all they want really.

Ergo they can't deal with any form if constructive criticism either. It's not a balanced relationship. I am generalising and there are good people out there but don't underestimate social conditioning.

MrsJeanLuc · 22/08/2025 08:10

C95 · 22/08/2025 00:02

May I ask why you would do this?

Not being goady!

Why would you give him the benefit of the doubt. There is no doubt, he's a negging walking bell end :)

No shades of grey in your world then 🤣🤣🤣

Returnofjude · 22/08/2025 07:51

He’s thick
He’s got a shitty relationship with (let me guess, his insane ex)
He asks weird and offensive questions

OP, I can hardly bring myself to dignify your question with a response

What is clear though is that you need to focus on building up your self esteem

TalulaHalulah · 22/08/2025 07:27

I don’t see why you would need to give up karate if you have another DC, so it’s a red flag that he expects you to, shows he doesn’t think about parenting as his responsibility as well.

In terms of the baggage comment, the person I am seeing used that term in connection with himself but more in terms of the emotional load of having been divorced, rather than his DC (whom he clearly adores and is connected with, also he is very respectful and supportive of their mum/his ex). I said that our experiences make us who we are and I wouldn’t think of it that way.

For me, the red flag is more what he says about wondering what he saw in you. That implies he thinks you should be grateful he deigned to date you. It’s an awful comment. You were right to get the ick.

i also agree with the posters who say don’t share bad experiences until you know someone well. You don’t have to explain your status as a single parent, it’s a common enough scenario these days. Protect yourself and your DC.

GargoylesofBeelzebub · 22/08/2025 07:24

as others have said dump him and tell him it’s because he has too much baggage.

Ooodelally · 22/08/2025 07:11

He obviously wants you to feel like he’s doing you some kind of favour by dating you. Absolutely gross of him. Block him and never look back…

dontcryformeargentina · 22/08/2025 05:51

He was negging you to undermine your confidence. I also sense cocklodger vibes.

Muffinmam · 22/08/2025 05:20

This would be a perfect opportunity to ghost this man. He can’t even drive his broke arse home from the movies. He’s not worth the effort to text.

Imisssleep2 · 22/08/2025 04:28

Tell him it's not going to work out, he has too much baggage and find someone more worthy of your time.

There is plenty of fish in the sea and I'm sorry you picked this one, don't be disheartened or put off, see it as a learning curve.

Those questions are Def odd and if he really feels that way not worth your time.

Never give up anything you enjoy for someone else, the right person will accept you and your hobbies etc as you are.

Personally I'd look at some one at least the same age or older we all know these men mature slower than women lol

AugustSlippedAwayIntoAMomentInTime · 22/08/2025 01:20

The hypocrisy and misogyny is rampant in this one.
Women have 'baggage' if they have children ... but not him?

Just wow.

I'd tell him to get to fuck and block him.

stayathomer · 22/08/2025 00:45

I know at the time shock prevents most of us saying anything, or the possibility of something dodgy happening, but you said you’re being short with him- I wish you’d said everything you said above - do you really think I should count myself lucky? How dare you call my kids baggage!! And you’re not the greatest catch yourself, how about you stop dating and help look after your kids!!

mmmarmalade · 22/08/2025 00:41

TLDR: What @Empress13 said!

I don't think he's ready to date anyone - by the sounds of it, not you anyway - surely you have to go into the dating scene with an open mind and an appetite to learn about and embrace whatever you find - how dense have you got to be to not understand that everyone who comes out of a marriage (or a LTR) has a long, complicated, personally meaningful story that will take some time to learn about and understand. He sounds like an absolute clot to me for so many reasons - why on earth would he be suggesting (a couple of dates in) that you give up a hobby you enjoy (instead of supporting and encouraging you)? Maybe he doesn't like the idea of you getting physical and grappling with other men? Baggage!? That's revealing isn't it? What a massive clanger! So he seems to think that your life should automatically be curtailed if you decide the have another child - that's not a very "supportive" and "equal" mindset is it?

Did he basically select this film in order to start airing his agenda and testing the water with you or was it something you choose together?

Give yourself some credit for getting out there because it seems to be what you want and no one says it's easy. This is the risk though isn't it - that you're not always going to meet guys you really feel confident about wanting to date seriously and you've got to learn how to exit in a way you feel comfortable with - it's not easy when you aren't used to doing it. I'd just encourage you to stand your ground, no need to feel you should make any excuses or be put on the back foot about your past or your current situation - this is you, this is your reality...own it. Maybe he was fine for a one off date but he doesn't sound like good building material for your next relationship especially if he can't express exactly what he is thinking and feeling - you shouldn't be left wondering or confused - good communication leaves you knowing either that you're on the same page or at least knowing where the differences lie.

Perhaps it's wise to not reveal the deepest parts of yourself until you get much deeper into a relationship - I know this might go against your natural instinct to be up front, open and honest. I think you're doing the right thing by tuning in to your gut instinct here.

DuckbilledSplatterPuff · 22/08/2025 00:28

nomas · 21/08/2025 18:23

Bad co-parenting relationship with ex 🚩
Controlling behaviour on self defence karate 🚩
Arrogance about your age / children 🚩

Plenty of red flag behaviours to ditch this one back in the sea.

Don’t feel defeated, be glad you have your boundaries intact.

I agree, he was particularly annoying in referring to her child and possibly her age as "baggage"

valentinka31 · 22/08/2025 00:07

you should say 'go on then - what did you see in me with all my baggage? I'm intrigued .. ; )'

I would. Rn.

valentinka31 · 22/08/2025 00:05

noidea69 · 21/08/2025 15:31

I'd have karate chopped him.

hahaha perfect

C95 · 22/08/2025 00:02

EdisinBurgh · 21/08/2025 16:20

Also giving him the benefit of the doubt - he might be very clumsy and undiplomatic and asking these loaded questions because he doesn’t have the confidence to say what is actually on his mind?

“I have baggage as a single parent and I wonder if you relate to this when it comes to dating”
”I’d love to have another child with you but would keeping up karate be a challenge when you’re pregnant?”

I think it’s worth having a frank chat with him to find out before you walk away!

Edited

May I ask why you would do this?

Not being goady!

Why would you give him the benefit of the doubt. There is no doubt, he's a negging walking bell end :)

MrsJeanLuc · 22/08/2025 00:01

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'?

Did you find out what he saw in you on the app? Or what he sees in "you and your baggage"? I would really want to know the answer!

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.

Empress13 · 21/08/2025 23:51

Get rid what a bellend

NiftyPrawn · 21/08/2025 23:47

This is “I’m the prize” mentality from him! Ladies, if you haven’t already, I urge you to look up The Burned Haystack Dating Method on facebook!

TenaciousDeeds · 21/08/2025 23:44

Returnofjude · 21/08/2025 15:32

I’d have just pulled over and calmly asked him to get out of my car

This!

Mmhmmn · 21/08/2025 23:33

Iamnotalemming · 21/08/2025 23:27

Classic negging. He is testing your boundaries to see what he get away with, trying to make you feel lucky to have got his attention, the Prince that he is.
Well, fuck that.

100% this.

Mmhmmn · 21/08/2025 23:31

Wow he’s negging you already.
Not a great sign of decency is it?

HowAmYa · 21/08/2025 23:29

You don’t have baggage. You have a life.
my DP is 9 years younger than me and he wouldn’t fucking dare even think of my DD as baggage. 5 years in and he STILL tells me he is the lucky one.

Hold your head high. Never ever see your past as anything other than chapters in your book of life. They are a part of you and your journey. He’s showing his true colours. He doesn’t deserve you whatsoever.