Dating a single parent, any advice?

[RomeoChallenger]

Hi all,

First time posting here but after any advice on offer please.
I'm a chap (in the gentleman sense who knows how a lady should be treated!) with no kids etc, and have recently been introduced to a thoroughly beautiful single lady who has two young boys. I've been besotted by her for a while now and would love to ask her out on a date.

Any advice? flowers and a nice evening meal out or is it better to do coffee dates etc in thinking about her childcare situation? (It appears her mum does the childcare on occasion, so unsure of notice needed etc or if this can be relied on). I obviously want to make an impression (hopefully a good one) but also want to be sensitive to her needs as a mum. Perhaps i'm being naive but reading some of the other dating threads here, it doesn't seem to be all that straightforward 😯
Also - would it be insulting to offer to pay for a childminder if mum wasn't free?

Other info that might be useful: she is a few years younger at 32, has a job and seems determined to be self reliant - i suspect because she doesn't want to come across as being 'indebted' which is fine, but i'm a little more old fashioned and of the position that if i suggest the date i should be paying. Plus i have a decent pay and bugger all to spend it on.
At the moment i haven't acted on anything, in part because i wanted to be sure and not bugger anyone around.

Before anyone mentions, i'm aware that if things go well longer term there is the kids. I've thought about it and happy for that to be the case, but one step at a time and all that... I just need the initial advice on dating.

Cheers in advance for any help.

Do you work near her? If so I'd suggest a lunchtime coffee date as the ideal first date (for anyone.)

Paying for a childminder - not on any initial dates. If things went well and you were a couple, then yes.

Can I ask how old you are? Your mention of being old-fashioned and some of your language choices are coming across as if you are late 50s, maybe early 60s?

Ask her out and then she can decide on her childcare! I wouldn't get a childminder, (a stranger in just to look after my children whilst I went out) and I think a lot of other mothers wouldn't either. Hopefully her mum would help out.

She sounds very independent, let her sort it for herself. You seem worried. Try and relax, you don't want to put her off!

I agree day time coffee date. Lots of people don't like to eat on first dates!

Woah there! Slow down. First things first: get to know her a little bit before worrying about babysitters etc. Does she show any interest in you at all?

Slowly, slowly, catchee monkey Bon chance!

Cheers guys.

Pocketsaviour 😂😂 not in my 50's. A very young minded 37 but as I say, a 'chap'. I just have a love of good words, good manners and periodically a liberal dash tweed 😬

Good points on the childminder.

Yes loveyoutothemoon guess I am panicking a bit, a date is still a date afterall and the butterflies are there

I know shes interested 😀

Chill! Good luck.

Good luck Romeo!
Can you let us know if she agrees to go out with you? I love a good romance , me!

Agree with pps re childcare. I'd say coffee/ lunch first. As to you wanting to pay, choose somewhere like a coffee shop that does sandwiches if you think she hasn't got much money for eating out. That way she won't feel she's either obliged to pay more than she can afford to be independent, or only able to attend cos your paying. And if you do offer to pay the bill it won't feel like charity.

Well, if it doesn't work out then bear in mind that my divorce will be through in about 3 months...

@ Thomas

Thanks ThomasRichard, always good to have a planB 😀 Guess if it doesn't work out she might end up posting here about awkward first dates or something so it'll provide you guys with some amusement at least 😂😂😂 (now paranoid that she does read/post here 😕)

Ofc Northernnights I'll post if all goes well, otherwise see above!

A lunch date sounds less formal for a first meeting so I'd suggest you ask if she wants to go for coffee and maybe lunch.

You can of course say, I'd like to ask you out. What suits you best coffee or a meal? Whatever suits you best as I know you have to work round the kids.

Or words to that effect (being careful not to make the kids sound like an inconvenience though).

Wow I am happy to read this thread, it gives me hope :) I am also 32 myself with two little ones and although I am far from been out there again, I have been thinking how I am going to rebuild my life.
For me, I will have time for myself when the children are with STBXH. That would be the ideal time to invite her out. But if the children's father is absent and she is the caregiver 24/7, I would say start with a couple of coffee dates while kids are at school and let her know that you would like to invite her for dinner some time. She will tell you what works best for her and if she is interested. I dont think offering to pay for a sitter would be welcome unless she says something along the lines of not being able to afford.
About paying for the meal, it is nice that you do but listen to her if she wants to go Dutch. I always assume 50/50 and take my credit card out when the bill comes. Sometimes I want to invite friends and they let me. Other times someone pays for my lunch and I accept. Sometimes I don't. It depends on the situation, reciprocity and the relationship between us.
Kids is a big one. How old are they? I would expect some implication from my partner in their lives. The younger they are the more. If they are teenagers I could take a friendly/uncle relationship as enough. If they little, like mine, my partner should become a second father and love them as his own. So you need to think very well about it before getting any further.

Good luck OP!

Yes I would ask her out for a coffee first on a lunchtime/late morning then if it's all going well you could always grab lunch too, but there is no pressure/expectation for anything more than a coffee.

I am a very independent single mum too and would be bit uncomfortable with someone buying dinner etc for me on a first date, but a coffee would be fine.

You sound very thoughtful, good luck

torontonion - thanks. Assuming you hail from sunny Canada? Lovely place.

They are young, 2 & 4 yo

Really appreciate all the advice people, i think i've done my usual panicking about every eventuality when of course a classic and simple approach would suffice. Guess i'm just keen come across well and not mess up what is a promising opportuntiy with a beautiful person.

I meant to also address the paying for a meal thing.

If she says "Shall we split the bill" and you say "No, I'll get it" and then she says "Ok, thanks very much" then great, you pay.

If she says "No, I'd prefer to go halves" then you go halves.

If a man made a massive deal that he insisted on paying - if he ignored my wishes to split the cost - it would REALLY put me off.

Aww I love a good love story I don't think my partner has ever took me on a date.... I'll shall be bringing that up later on, agree with everyone, nice slow approach at first but still turn the charm on with a bunch of flowers.

Good luck and keep us informed

Completely agree with pocketsaviour about the bill thing.

Childcare this early is not your concern so don't go there

Likewise re avoiding dinner as a first date. Coffee/ cheeky drink.

Re paying the bill - offer and take her lead. If she insists on splitting then let her. Or (if the date has been good), say she can treat you next time.
Re her independence, this is how you get round it. If the dating moves to dinner then when it's her turn to pick up the tab, let her pick. When it's your turn to pay you pick the restaurant. I dated a guy in my twenties who earned vastly more than I did. I could never have let him pick the bill up all the time. So I took him to restaurants I could afford, and he did the same. Perfect.

Finally, don't come on too strong too soon. You sound lovely and genuine but without knowing her circumstances, too much too soon could scare her off. Listen to what she has to say. Observe and respect her boundaries and go at her pace.

Good luck OP!

I'm going to be a lone voice I think, but you have asked for any opinions and perhaps it will be helpful on the off chance that this woman is like me. I know on here I'm not the only one

You come across - to me - as patronising. So watch that with her.

You want to pay for someone else: you're an old fashioned gent.

She wants to pay for herself: you start deciding that she doesn't like to feel indebted, that she "seems determined to be self reliant".

Go go little lady for being - oh, a normal woman?

Maybe she pays for herself (where are you even getting these assumptions from?) because - that's just what women do.

Look, I may get called out by others - and you! - for being too harsh. But I genuinely mean it helpfully. I've done a bit of online dating and the "I pay because I'm a gentleman" type really puts me off.

I never want a man to pay early on - simply because, why should he? I actually find it unfair on men, I believe in equality and I want men to break what is to me, old fashioned crap, as much as I want to break it myself.

I'd find it really offputting if I found out a guy thought about - and posted about! - this stuff before even asking me out!

Just... ask her for coffee.
Offer to pay not because you are "old fashioned" or earn more. (if you even do) Offer to pay because it's a kind and generous small gesture.

But let's just throw this in; maybe - SHE will offer to pay. In which case, how about you just saying "thank you"? I had a couple of online date meets where I really didn't see a match because of equal paying / splitting. It's not "old fashioned" when you get to the insisting rather than offering stage - it's just rude. If she wants to pay, she just does. She's not "determined to be self reliant" - she's just an ordinary woman going about her day.

Leave any discussion about paying for babysitters til down the line a bit.
At 2 and 4, she may only feel happy leaving them with her parents - and have no cost.

By the way, I'm a single parent who happily enjoys her boyfriend paying for things sometimes, even though I earn 3x what he does. I love that he wants to arrange things and treat me sometimes. I wouldn't date him if he thought men had to /ought to pay. He'd just not be a personality for for me.

Totally agree with TooSassy on longer term strategy of paying an equal number of times, but each person choosing the date according to their means.
My boyfriend cooks at home for me, I pay for the fanciest restaurant in town... occasionally!!
It works