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I'm a single father and I'd like to approach another lady at my son's school, but I don't know how

Tagged as: Big Questions, Crushes, Health<< Previous question   Next question >>
Question - (14 March 2013) 6 Answers - (Newest, 16 March 2013)
A male United Kingdom age 41-50, anonymous writes:

I have an almost crippling level of shyness which has never really been a problem for me until recently.

I am a single father and have been happily so for a while now. Recently whilst collecting my son from school I noticed a woman and really want to find out if she is single too, but even if I found out I can't see myself ever approaching her. The problem being she is the first woman I have seen that I really fancy and desperately want to approach her.

We have made eye contact a few times but I worry she will think I'm some crazy stalker who keeps staring at her. I'm not saying it's love at first sight, but I see her nearly every day and she literally takes my breath away. But what if she's not single? What if I come across as a freak? What if she isn't attracted to me?

I so need help.

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A reader, anonymous, writes (16 March 2013):

Why ask a parent you do know, when you want to get to know the one you don’t know?, I understand the anxiety, I am a single parent I talk to parents whose children are in all year groups so I personally don’t think it that much of an issue that her Child is not in the same class as yours, ok so I am a female and we love to chat, but I feel that this is the best way to have a non-pressured chat, where you can test the waters. Unless you subtly flirted with her and she gave you instant signals that she was interested, asking questions would be the best way and most natural way to approach her, if you come across as full on and it doesn’t go well, unless your child is in his final year, you would still have to see her everyday. Good luck

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A reader, anonymous, writes (15 March 2013):

Hi, original poster here.

That, approaching and asking a question about school, would be all well and good. But our kids are in different classes so it would seem weird me asking her when I could just as easily ask a parent I DO know.

@Cerberus

I actually checked today and there is no ring. So, I think some time next week I may take a deep breath and say hello...

Ha, I'm suffering anxiety attacks just at the thought of it!!

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A male reader, anonymous, writes (15 March 2013):

Hi original poster here.

That, approaching and asking a question about school, would be all well and good. But our kids are in different classes so it would seem weird me asking her when I could just as easily ask a parent I DO know.

@Cerberus

I actually checked today and there is no ring. So, I think some time next week I may take a deep breath and say hello...

Ha, I'm suffering anxiety attacks just at the thought of it!!

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A reader, anonymous, writes (15 March 2013):

Stop over-thinking things and just ask her a school related question. "Do you know if the school play is on late again this year?" or other such question. Start up a conversation and be on speaking terms for a few weeks at the school gates.

If she doesn't have a wedding ring on her finger then just assume she's single and approach it as such, she'll let you know if she's spoken for.

OP you have the best excuse to ask her out too, I'd tell her about a thing you're bringing your son to, an adventure playground or other such thing and say in passing that she should come along some time with her kid too. Use a play date as a way to get to know her and then maybe ask her out properly to a gig or something.

Most of all though just talk to her OP, the longer you leave this the more you'll burn it out in your head and the more fear will build. Just take the chance, assume she's single if she doesn't have a wedding ring and work from there.

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A reader, anonymous, writes (15 March 2013):

For single parents the school gates are the most appropriate place to meet potential partners as you have your kids in common.

As a parent, the school is a great place for any conversation you ask questions like “do you know where I can find out what is on the school dinner’s menu?”, “Where do I hand in comic relief donations?” “Do you know when they return back to school after the Easter holiday?” "My child’s been invited to a little girl’s party and I don’t know what to buy them as a present, she is your child’s age, and what would you suggest?” Where did your child’s sports bag from as I’ve been looking all over town for one” “Do you know any cub scout clubs in the area for kids my child’s age? ” “ I want to sign my child up for art club, does your child go?, is it good”

Once you break the ice, every time you see her you should be able to say hi, and make small talk, sit next to each other in assembly’s, school plays, sports days then take it from there. Good luck.

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A female reader, oldbag United Kingdom +, writes (15 March 2013):

oldbag agony auntHi

You can't keep staring, you just need to find a reason to approach her. As you see her daily and at the school there must be a topic you can open a chat with.

Maybe ask her if the Easter holidays start on Friday..or if she knows if they get let out early that day.Its a good topic to open with this week and you could then ask if she is going away with her husband and kids for the break...and say what you will be doing.

Just take a deep breath and do it,it doesn't sound creepy it's just school gate banter

Good luck

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