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Original poster

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:
Francestein · 21/08/2025 15:23

Ick central. What a weirdo. How dare you have an actual life outside of him?

Returnofjude · 21/08/2025 15:28

What I can’t believe is what you feel the need to even ask Op?

Your standards must be in the gutter to be questioning this

Returnofjude · 21/08/2025 15:29

Not only utterly weird OP

He doesn’t exactly sound the sharpest tool in
the box

The film you’re talking about, The Drop, hasn’t been shown at my local odeon for weeks now… released quite some time ago. So have you seen him since?

noidea69 · 21/08/2025 15:31

I'd have karate chopped him.

Returnofjude · 21/08/2025 15:31

You’re 27
You have obviously only recently come out of a horrible relationship
and you have multiple presumably very young children

Just settle in to newly single life op and enjoy it. Lots of time for men!

OtterlyMad · 21/08/2025 15:31

lol he clearly thinks of himself as a catch
🚩 🚩 🚩

Returnofjude · 21/08/2025 15:32

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

SummerHouse · 21/08/2025 15:34

Him: "did you wonder what I saw in you with all your baggage"
Your response: "no, I am fabulous. I am only wondering what I saw in you with all your weird and loaded questions"

MounjaroMounjaro · 21/08/2025 15:34

Ugh, he's horrible! What a twat thinking your child is baggage, particularly when he has one himself.

One thing, though, is that I think it's a mistake to talk to someone new about bad relationships. It can imply you don't have boundaries. I'd hate his eyes to light up at that thought.

Nookfoot · 21/08/2025 15:35

I think he was asking if you want more kids. I.e. the "baggage" would be OK for someone who wants a family life, another pregnancy might mean stepping back from karate.

Very clumsy and not a good sign that he can't just say what's on his mind though.

HellEvenDorisDay · 21/08/2025 15:35

Trust your instincts. Better to reject someone now than a few more dates in and it’s harder to disentangle yourself from

Jojimoji · 21/08/2025 15:35

Returnofjude · 21/08/2025 15:32

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

Exactly.

"Did you ever wonder what I saw in you?"
" You can walk from here"

Largeherbivore · 21/08/2025 15:36

To give him the slight benefit of the doubt, he may be a bit sore that his dating pool is smaller than he expected because many children women won't touch a man with kids, so he could well be projecting. But he's definitely not diplomatic and you can probably do better.

travailtotravel · 21/08/2025 15:36

Isn't it good when they expose themselves early so you can move on quickly!

Returnofjude · 21/08/2025 15:37

Nookfoot · 21/08/2025 15:35

I think he was asking if you want more kids. I.e. the "baggage" would be OK for someone who wants a family life, another pregnancy might mean stepping back from karate.

Very clumsy and not a good sign that he can't just say what's on his mind though.

Bloody hell that’s a kind interpretation

MounjaroMounjaro · 21/08/2025 15:39

Maybe you should have said, when asked why he was interested, "Well, I guess you must have realised you were punching above your weight, but thought you'd give it a go."

Bibonelove · 21/08/2025 15:42

If he's like this on the 3rd date imagine what he'd be like after 6 months , Red flag written all over it, block him

PudgeJudy · 21/08/2025 15:44

Returnofjude · 21/08/2025 15:29

Not only utterly weird OP

He doesn’t exactly sound the sharpest tool in
the box

The film you’re talking about, The Drop, hasn’t been shown at my local odeon for weeks now… released quite some time ago. So have you seen him since?

How do you know which film she went to see??

Muffsies · 21/08/2025 15:46

MounjaroMounjaro · 21/08/2025 15:34

Ugh, he's horrible! What a twat thinking your child is baggage, particularly when he has one himself.

One thing, though, is that I think it's a mistake to talk to someone new about bad relationships. It can imply you don't have boundaries. I'd hate his eyes to light up at that thought.

Exactly, women talking about being treated badly by multiple ex partners is equivalent to men talking about their 'crazy' ex girlfriends. It's a red flag both ways, sadly.

It's fine to say you've had previous relationships that didn't work out and you've learnt from the experience, but it's best to keep the details private until you know someone better. That information can either be used to test how vulnerable/manipulatable you are, or will just get thrown back in your face when they want to hurt/discard you.

EmeraldShamrock000 · 21/08/2025 15:49

Never tell a new guy about bad experiences in a relationship, it is a green flag for fuckwits.
Deep conversations are better in deeply connected relationships.
I think he believes you're far game for mean banter, a bit less than him.
Have a chat with him, he might be just clumsy or could be a prick

waterrat · 21/08/2025 15:51

I got a shiver reading that.

He is negging you - working out if he can abuse you.

he is not clumsy, jesus christ. He used the word 'baggage' - get as far away as you can very fast.

CharlotteLightandDark · 21/08/2025 15:53

MounjaroMounjaro · 21/08/2025 15:34

Ugh, he's horrible! What a twat thinking your child is baggage, particularly when he has one himself.

One thing, though, is that I think it's a mistake to talk to someone new about bad relationships. It can imply you don't have boundaries. I'd hate his eyes to light up at that thought.

Agree. It can make you look vulnerable or like you lack boundaries/good judgement even if that’s not the case.

it always makes me cringe when shows like First Date encourage people to spill about their insecurities/past bad experiences on the first dates, it’s not a good idea!

AbzMoz · 21/08/2025 15:58

It’s pretty obvious that this is not the one for you OP. Sounds like he’s revealed himself as someone who enjoys negging and thinks you should now and forever be grateful for him gracing you with his presence..
trust your gut

Xyloplane · 21/08/2025 16:05

Throw this one back OP. He wants you to give up your hobby and to start being more grateful that he deigned to pick you given your unacceptable levels of “baggage”. He wants to grind down your confidence. And why on earth are you dropping him off? He can get the bus.

Returnofjude · 21/08/2025 16:06

PudgeJudy · 21/08/2025 15:44

How do you know which film she went to see??

Show quote history

Because I saw it…. Single mum getting back in to dating for the first time