Should I ask her out? Or should I chicken out?

Miscellaneous and Personal Stuff I Must Share
1

So, there is a woman that I work with at L.L.Bean whom I like. Like as in the “I’d like to ask her out on a date type thingee” kind of way, as opposed to the like as in the “Gee, it’s really nice to chit-chat with you during breaks and at lunch.”

I’m 33 almost but not quite yet 34, she’s 23. She has a 3 year old daughter. She is also sorta maybe on welfare, I don’t know all of the details, but she has mentioned going to the local food bank, and having to skip dinner and breakfast. Meanwhile I have money to smolder, if not burn.

Oh, her name is Charity. And she’s a different Charity then the one I mentioned in an earlier thread.

We’ve talked a good bit at work, we’ve made each other laugh, I haven’t made a fool out of myself in front of her. She’s done the whole “touching thing.” By that I mean that today when they announced the afternoone update and strech break, I was in front of her and she was playfully shoving me from behind. I didn’t reciprocate, for reasons I am unable to recall at this time, but which probably include my fear of my hand landing in the wrong place, and my general fear.

I want to ask her out, but when I think about it, then the issues that arose with my ex rise up and settle uncomfortabley on things. I’m sure I have a thread about my ex on the board, I’m just not gonna search for it.

So, should I go for it, wait, or send it up?

It’s weird, sitting here typing this and thinking about the situation makes me upset, because on the one hand I have these feelings, albeit it fairly new about Charity, but then the feelings and issues about my ex come up and roil around.

Sigh

Advice is welcome.*

*If you are thinking of making fun of me, knock yourself out.

2

I’d say go for it. :slight_smile:

3

Be brave–ask her out! Women like that! And you can always act like it was just a friendly thing if you get turned down (which I doubt you will–sounds like she’s sending signals).

4

Ask. It is better to know now than to always wonder.

5

Go for it!
Only one thing: if she’s on welfare, she may not have the freedom to get whoever is babysitting for her to do so for a date, so be prepared in case she mentions that.

6

Carpe deim.

No fish were harmed in this post.

You regret more the things you have not done, than any you have.

Trust me I’m old, and have not done things I should have.

7

See now I’d say, “Don’t do it”.

Mostly because although I do have a reasonably commited ‘carpe diem’ attitude, I also have a ‘whatever will be, will be’ attitude.

My hope for you is that she makes the first move.

Aw, to hell with it, ask her. You know you want to.

(A couple of fish were harmed in the writing of this post…but they’re better now. Mostly.)

8

I’m confused, how can she work there with you & have to skip two meals a day? I must assume that she makes enough there that she won’t need welfare, or they won’t pay her as much, or she may simply need it for the medi-cal (Didn’t Clinton drop welfare years ago?).

Sounds like she needs rescuing or wants to play that part, so maybe you can be the hero?

9

WSLer, ask her. Even if she said “no” you aren’t any worse off than you are right now. I think it sounds like she is interested in you. As noted above, offer to pay for a sitter perhaps or be willing to include the child in your activities.

Best Wishes

10

Definitely ask.
Looking back, I suggest far more people regret the times they didn’t ask, than the times they did - whatever the results.

11

Go for it !

12

And for a different point of view…

Poor single mom don’t want to be poor single mom. How far are you willing to go down this road? If the answer is “all the way”, then viola, instant family. Things can happen very quickly when one of the parties is motivated.

Also, be aware that the little child has a daddy somewhere. An unknown quantity?

I’m not saying don’t ask her out, I’m just saying be aware of what you’re willing to involve yourself in.

Cheers.

13

Another vote in the “Ask her” category.

14

Well, somebody has to say it: What’s your company’s ruling on employee fraternization et al.? If there’s no problem officially, and you think you can pull this off without getting fired, I’d say go for it.

15

Go for it.

Hey one of us has to do it asI always chicken out and then regret it.

16

Yep. Go for it. Take her back to that little corner downstairs where they keep the backpacks (at least there was one a couple of years ago…) and ask her on a date. If she shuts you down, noone else will have seen it. :cool:

17

Chicken out! Chicken out!

Just kidding, WSLer, give it a shot.

18

Man, he’s just wondering if he should ask her out on a date, I don’t think marriage has been brought up yet.

Go for it. Single moms need company too. Maybe offer her a couple bucks for babysitting money.

19

“ask”
“chicken”

Is “eat” an option?

20

Well, how long have you known her? Not that it matters that much; fer chrissakes, ask her out for coffee or something! Low-key.

Of course, I’m a big hypocrite myself for the most part, so you don’t have to listen to me.