Asking out the impossible

[chuffedasbuttons]

Firstly I chose relationships for sensible answers! Bear that in mind if you could please!

I'm a single divorced Mum of 2. My younger is year 6. We have had big trauma and they don't see their dad because he got a criminal record. We are good and in a good place. We are happy despite big upheavals - house and school moves.

My son will finish primary this year. He's been there since we moved.

I fancy his headteacher - a suitable and single person. It's a bit long and complicated and outing but basically a few years ago - he totally checked me out, before we were at the school. I just know.

What on earth do I do at the end of the year? I've not even seen him this year because of Covid. I haven't bothered thinking about him because he is who he is but as the primary stage nears the end.... I'm constantly thinking about the what's and how's.

It all just seems so inappropriate but I'm now grown up enough to know that when there is a chemistry, it's worth a look!!
I've ignored this because I'm not comfortable with the parent /school scenario
.....

It's becoming a bit of an obsession now the end is nigh. I'm annoying myself.

Watching with interest as in a similar situation myself! Big crush on headteacher developed after they started helping with social distancing measures during drop off and we started exchanging pleasantries. We’re both single and they seem to like me enough to give me a smile every day. If it were someone at a hobby club or in social situation I’d probably ask them for a drink. But it’s not - it’s the blooming headteacher so obviously awkward. Anyone have experience of similar situation?

It's one thing him finding you physically attractive a few years ago, quite another to consider a relationship with you.
If you are looking for a partner, maybe widen the field a bit.

Inappropriate if your child is still at that school.

I'd go back to thinking about it less and try hard to stop obsessing over it.

If you don't, you'll likely approach this all wrong and possibly end up getting your feeling unnecessarily hurt. I get that it's been a bad year and having a crush is a welcome interest, but:
Is this all based on just that one time he checked you out?
How many interactions have you had with him?
Do you definitely know he is single? He could be dating privately, he could be seeing someone - or even in a relationship by now.

You know the ole fancying a teacher thing. The river loves the moon but the moon sees many rivers.
As a professional in the role, he sees what, 500 parents at least.
It's a fantasy, he is paid to care or at least be professional enough go seem to care. He must probably doesn't fancy you.

Oh dear, I don't think because your child's head teacher smiled at you means he's interested in a relationship. He's smiling because he's doing the meet and great thing not the checking you out thing.

It's literally his job to - amongst other things - be nice, reassuring and positive to the kids parents.

How could you possibly know he is single if you haven't seen him all year? A bit of a passing interest a few years ago doesn't mean anything. Anyway, even if you're right, you've still got 8 months before your child leaves the school - it's a bit early to be making plans!

I wouldn't dream of doing anything whilst DS is still at school. As it's his last year, I am thinking ahead.

When he checked me out, it was not at a school event and before we attended. We haven't been there since year R. So he wasn't at school and I wasn't a parent.

It turned out I ended up being a parent and I hardly see him as I don't do school runs.

I am torn between doing nothing ever because it feels weird OR somehow doing something at the end of summer when I won't be crossing paths ever again.

He can always turn me down and I wouldn't be bothered.

He can always turn me down and I wouldn't be bothered.

Who are you kidding?

@Cautious47 awkward it is indeed!

@Ifailed I have and do date sometimes when I have the energy. Online is such an effort but I haven't come across anyone I fancy.

@LumpyPillow he is single. School community is pretty small and of course people talk.

Be honest are you attractive ? Maybe he just wants yo look but not touch... the soultion seems simple just ask and its either a yeah or a nah

@Ifailed I'm not kidding anyone. Dating and life have given me a pretty tough skin. I'm a big girl hence I want to ask him out.

I just don't know how because of the situation.

@MummyShah369
Yes I think we are both firmly in the attractive 'especially for our age' group.

Mid late 40's

Many mothers fawn over him from what I hear. I think that's different.

Once your son has finished at the school there is nothing stopping you from asking him out. You're both single and attractive and you don't seem too bothered if he turns you down
Go for it I'd say - you have nothing to lose.