Dating a single mom at preschool

[Anonymous]

There's a single mom I think is cool at my kids preschool. Any tips to show interest or ask her out? So far we've gotten acquainted at birthday parties and say hi some mornings? I'm new again to the dating game.

[Anonymous]

Are you single too?

[Anonymous]

Anonymous wrote:Are you single too?

Yes!

[Anonymous]

Play date with kids?
Ask her out for covfefe?

[Anonymous]

Just no. It’s like dating at work but worse because your kid is involved

[Anonymous]

Send her a shirtless bathroom mirror selfie. I hear women really like those!

[Anonymous]

Play date with kids for sure

[Anonymous]

No! Don’t do it!

[Anonymous]

Anonymous wrote:Play date with kids for sure

Using your kid...not cool.

[Anonymous]

Assuming you drop the kids off and then return later, "hi ____, getting a quick coffee before heading to the office, how about if you join me"?

[Anonymous]

Anonymous wrote:Assuming you drop the kids off and then return later, "hi ____, getting a quick coffee before heading to the office, how about if you join me"?

Would saying your hair looks nice show I'm interested

[Anonymous]

Stop listening to these pearl clutches. It’s perfectly fine to ask her out.

[Anonymous]

Anonymous wrote:Just no. It’s like dating at work but worse because your kid is involved

+1. I would never date a parent at my child's school. I would never date a co-worker. Same reasoning. Also, I hate to feel like I am being looked over as potential dating material in every environment I am in. While you may think it's some sort of compliment, the woman has to make all kinds of calculations even if she likes you about how you may react if she says yes/no or if you have a relationship that doesn't work out. I say this as a woman who has been asked out at work and when you say no, the guy retaliates, sometimes openly, sometimes subtly. Subtly is actually the worst because it is very hard to call out. Also, you don't know whether they are talking you down to other people.

It's the same in the parents at pre-school environment. If you like her, be her friend without any ulterior motives.

[Anonymous]

Are you the same guy that's posted different iterations of this question since September? If so, grow some balls first. Your inability to make a decision without crowdsourcing and act on it are both a major turnoff.

[Anonymous]

You can ask her about a playdate. Or just ask her out. She may be dating someone too, so just be prepared for that. A playdate would allow you to get more information. If she's been friendly at the birthday parties, that's a good sign.

Also I don't think it's the same thing as work at ALL. If it gets awkward, oh well, the end of year party will be weird. Then you move on. It's not like sitting in a meeting next to someone who saw you naked.