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Relationships

Mumsnet has not checked the qualifications of anyone posting here. If you need help urgently or expert advice, please see our domestic violence webguide and/or relationships webguide. Many Mumsnetters experiencing domestic abuse have found this thread helpful: Listen up, everybody

Should I ask him out?

26 replies

AnotherSchoolRunMum · 16/05/2026 12:50

I'm 31, single mum to 2 DC. I separated from exH a year ago, we were together for over 10yrs before that so the last time I was dating was in my late teens!

There is a man I really like and I feel so out of my depth with dating these days I don't know what I should do! He's a single dad, his DD is in the same school year as my eldest DS. We've known each other in passing for a few years as the DCs went to nursery together but it's only since we've seen each other more regularly on the school run that we've started to talk a bit more.

He's really great, seems so kind and thoughtful. He's a wonderful dad to his DD and very involved parent (50% custody since she was very young). I really admire his parenting style and how patient and understanding he seems to be with her. Everyone I know from the school group talks very positively about him (things along the lines of 'oh have you met Brian? Isn't he such a nice guy?' etc) he seems the kind of person who gets on well with everyone. Physically he's exactly my 'type' and I find him very attractive.

I see him a couple of times a week on the school run and occasionally when the DC are invited to the same parties etc. We've chatted quite a bit at a surface level (about DC, school, weekend plans etc) and the conversation always feels really easy. There have been a few times where it's just the 2 of us and I've felt there's been a connection with more intense eye contact and smiling but I could be completely making that up because I want it to be true!

The problem is I only see him for 5 minutes a couple times a week (sometimes less if we're late / kids are ill etc) and there isn't really a lot of opportunity to get to know him better. I have his phone number because our DC have attended each others parties and there was also a time where he asked if he could take a photo of our DC doing an activity at school together (think sports day / school fair) and said he had my number so would send the pic to me after (which he did). Would I be completely crazy to text him and ask if he'd like to go for a coffee or something? I've never asked anyone out in my life!

I'm worried that if he says no it'll be really awkward and I'll have to avoid him for years until our DC leave school! I'm also in a nice little friendship group of school run mums which includes his DD's mum - we're not close but get along well enough. For what it's worth she is with someone new and has talked about setting her ex up with people before so I don't think there are any lingering feelings there but could still be awkward!

Any advice welcomed please, I feel like a teenager again 🙈 Sorry this is so long!

OP posts:
Mysticguru · 16/05/2026 12:59

People cannot help who they are drawn to. If you feel there is a connection between you then suggesting a chat over coffee isn't outrageous.
Who knows where it will lead. Could be nowhere or somewhere.
At least you will know one way or the other.

Endofyear · 16/05/2026 12:59

Yes go for it! Just a casual text saying do you fancy meeting up for a coffee next week? If he says no, he'll probably make an excuse like sorry, I can't, really busy with work at the moment, then you can say ok, no problem, catch up with you soon. Then just be your normal polite and friendly self when you see him!

But - there's a good chance he'll say yes and it could lead to a lovely relationship! I'd take the chance, you have nothing to lose and everything to gain! Be brave and seize the opportunity!

NowStartingOver · 16/05/2026 13:01

Yes, you should. Ignore the trope "if he's likes you, you would definitely know about it".

CaffeinatedSeagull · 16/05/2026 13:18

Go for it… us guys can also find the whole asking out thing awkward too. Suggest a coffee and see how he reacts and if he suggests a place and time.

FloydPink · 16/05/2026 13:34

He could be thinking the same. He may not, but unless you ask you would never know.

Ilovecoffeeme · 16/05/2026 13:40

Shy bairns get nowt as they say. Go for it. No harm in asking

Goditsmemargaret · 16/05/2026 13:48

I was all on for asking until you said it would be awkward if he says no. Put that right out of your head!

The very very very worst thing that will happen if he says no is that he will be very flattered and privately impressed that you showed initiative. Plus you'll be able to say you took a risk and went for something.

WillieBanjo · 16/05/2026 13:51

I think, as a single guy on the school run, there is a much greater risk to him asking you out and getting it wrong than the other way around. My friend is in this position, and no one even talks to him, and he has even had problems scheduling play dates with his daughters' friends. I know there is no way he'd approach anyone from school for that reason.

You should go for it. If he likes you, I am sure he will be over the moon,

Thebargeonthecanal2002 · 16/05/2026 16:55

I’m sure you go for coffee with females too. So ask him casually but not as in “A date” just coffee & a chat & see how it goes. Hopefully then another coffee date will follow & go from there. From there you will be able to gage whether he feels the same, or just wants friendship. Good luck!

INX · 16/05/2026 17:09

Bit weird that his ex talks to other school mums about setting him up with someone.

In fact it sounds like the script for a kids's movie. All we need now is for his kids to want to do the same 😁

I'd ask him out for a coffee and see what he says.

Mumlaplomb · 16/05/2026 17:32

I think I would drop a hint eg “I really want to see x film” and see if he takes the bait.

CountryGirlInTheCity · 16/05/2026 18:22

Mumlaplomb · 16/05/2026 17:32

I think I would drop a hint eg “I really want to see x film” and see if he takes the bait.

Nooo don’t do this OP! There’s every chance you’ll still have no clue whether he likes you or not.

I’ve been with DH for 37 years and he still wouldn’t necessarily pick up that ‘I’d like to see x film’ means ‘please will you come with me to x film’! He’d probably just say ‘Oh would you Love? I hadn’t even noticed it was on.’ Or something equally oblivious! And he’s a kind, lovely attentive DH.

In my experience hints will get you nowhere, men generally like straight talking and to know where they stand. Just ask him to go for a drink with you. If he says yes, you know he’s probably up for a date and if he says no at least you’re not wasting any more time dreaming about it. Don’t be awkward the next time you see him, just smile and act normally and it will probably all be fine!

Georgiapeach21 · 16/05/2026 18:27

I would casually start a conversation with him on wattsapp and see how the conversation goes! You might get an idea from that and then can always ask!

why am I invested in knowing how this ends 🤣❤️

AnotherSchoolRunMum · 16/05/2026 18:32

Thanks for the replies everyone, pretty unanimous that I should just ask him!

It's interesting to hear the male perspective as well, I hadn't considered that there's more risk on his side from asking me than the other way around.

I think I will take a few weeks to work up some courage (and try to subtly judge his interest in the meantime) then maybe ask him at the end of the school term - that way if he says no at least I won't have to see him the next day! 🙈

OP posts:
AnotherSchoolRunMum · 16/05/2026 18:35

INX · 16/05/2026 17:09

Bit weird that his ex talks to other school mums about setting him up with someone.

In fact it sounds like the script for a kids's movie. All we need now is for his kids to want to do the same 😁

I'd ask him out for a coffee and see what he says.

I get the impression from her that he's a bit introverted and doesn't really put himself out there, hence the mention of setting him up with people. It's not the impression I've got from him (he's always quite happy chatting with the other parents) but maybe he's more reserved outside of that setting?

OP posts:
AnotherSchoolRunMum · 16/05/2026 18:35

Georgiapeach21 · 16/05/2026 18:27

I would casually start a conversation with him on wattsapp and see how the conversation goes! You might get an idea from that and then can always ask!

why am I invested in knowing how this ends 🤣❤️

I will update if I'm brave enough to go through with it! 😂

OP posts:
Delphiniumandlupins · 16/05/2026 18:42

I think asking him for coffee at a fairly specific time is a good idea, so "next week" or "before sports day" rather than "sometime". He can come up with an excuse if it's not convenient and neither of you need to feel awkward.

INX · 16/05/2026 18:51

Mumlaplomb · 16/05/2026 17:32

I think I would drop a hint eg “I really want to see x film” and see if he takes the bait.

Christ, I read that as "I really want to see a sex film"!! 🙈🤣

Bit forward, but why not 🤭

StarlightLady · 17/05/2026 07:26

AnotherSchoolRunMum · 16/05/2026 18:35

I will update if I'm brave enough to go through with it! 😂

Go for it OP. Way back someone (male) said to me that they were really flattered because l was the first ever woman to ask him.

Dery · 17/05/2026 08:25

“Delphiniumandlupins · Yesterday 18:42
I think asking him for coffee at a fairly specific time is a good idea, so "next week" or "before sports day" rather than "sometime". He can come up with an excuse if it's not convenient and neither of you need to feel awkward.”

Agree with @Delphiniumandlupins. This is a good way to go it you can. Good luck, OP! Nothing ventured, nothing gained. I suspect he’ll be chuffed you suggested it, whether or not he accepts your invitation.

Frillysweetpea · 18/05/2026 21:21

AnotherSchoolRunMum · 16/05/2026 18:32

Thanks for the replies everyone, pretty unanimous that I should just ask him!

It's interesting to hear the male perspective as well, I hadn't considered that there's more risk on his side from asking me than the other way around.

I think I will take a few weeks to work up some courage (and try to subtly judge his interest in the meantime) then maybe ask him at the end of the school term - that way if he says no at least I won't have to see him the next day! 🙈

No, no - don't wait! You don't know who also might have their eye on him - just go for it!

Gossipisgood · Yesterday 10:38

Next time you see at school just say ' Hi, I've not got time this morning for a chat but it'd be nice having a catch up, fancy going for coffee sometime, I'm free this weekend if you do' see what his reaction is & go from there. Or you could be a bit more direct & text saying you've not seen him for a while, how is he & does he fancy a catch up over coffee sometime. You've nothing to lose really so go for it.

StarlightLady · Yesterday 11:22

Gossipisgood · Yesterday 10:38

Next time you see at school just say ' Hi, I've not got time this morning for a chat but it'd be nice having a catch up, fancy going for coffee sometime, I'm free this weekend if you do' see what his reaction is & go from there. Or you could be a bit more direct & text saying you've not seen him for a while, how is he & does he fancy a catch up over coffee sometime. You've nothing to lose really so go for it.

This ❤️

UnemployedNotRetired · Yesterday 12:00

I'd take a more subtle approach. Invite him to something you are already planning to do and see if he wants to attend.

So, "on Saturday at 11am I'm going to be at the farmers market/cafe/whatever. Would be nice to have company if you're free and get to know each other a little better".

CurlyKoalie · Yesterday 12:17

UnemployedNotRetired · Yesterday 12:00

I'd take a more subtle approach. Invite him to something you are already planning to do and see if he wants to attend.

So, "on Saturday at 11am I'm going to be at the farmers market/cafe/whatever. Would be nice to have company if you're free and get to know each other a little better".

I agree with this. Try a meet up on a really public place so that either of you could just leave without consequence of it gets a bit uncomfortable.
I would definitely give it a go, take it slow. You will always wonder " what if?' if you don't.

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