I kinda like a work colleague

[Terminator]

I'm in my 30s and I kinda like a work colleague who is 10 years older than me, but she looks very young for her age. She's been single for a few years and she claims she always had bad luck with men.

Lots of customers try to hit on her, but she always says no. Sometimes, as soon as the customers leave, I like to tease her like: "You finally found the man!" or "Let me know when you guys marry, I'll be there!". She laughs but she's always like "all men only wants one thing".

She's very sweet and caring. Probably the nicest and kindest person you'll ever know. She loves everyone and always finds the bright side in everything. Some colleagues don't like her because they think she's too nice. But it also looks like she's very insecure.

I'm thinking of asking her out for a date, but how? I'm afraid she might go like "ew, you too only want one thing" or something like that. What would you do? Note: I'm probably not looking for a serious relationship with her. But I wouldn't mind going on a date and see what happens.

[Batya33]

I wouldn't risk it for just a date and I would be wary of anyone who makes such negative comments about men.  

I'd also stop teasing her about how men are attracted to her since this is a work situation.

[Andrina]

The majority of new dating situations don't work out, and then you have the awkwardness of having to see the co-worker you once dated on a daily basis. Not fun, especially if it ends with angry/bad feelings.

I'd keep dating outside of the workplace.

[smackie9]

I would just keep it casual and friend like at first. Build up a rapport so she can trust you and your intensions. Ask her if she wants to go out for lunch, or Uber lunch in. 

[yogacat]

I know you're teasing which is always fun but when you're interested in dating a woman, making references to her getting married to someone else could make her think you're not serious and just joking around. So, if you're really interested, stop teasing and ask her if she'd like to go out with you for dinner some time. 

[catfeeder]

I'd focus less on the asking and more on potential outcomes and how these could impact my work life going forward. If this is just a stop-gap job that you don't take seriously and will be leaving soon, that's one thing. But if this is a job you intend to keep for the foreseeable future, I'd hold off unless and until one of you gives notice to leave the job.

[ShySoul]

First, don't tease her like that. If you don't want her thinking that you want that one thing, then don't be saying things that could insinuate you are thinking along those lines. If she has had bad luck with men, and is getting hit on at work, then teasing her about it isn't going to come off well. It makes you seem like you are like those men.

Stand out and be different. Give genuine compliments. Do things to return the same kindness she is giving to others. Show her you are appreciative of the things that she does. Tease or laugh at the men who are hitting on her, how desparate they come off. Show her respect and sympathy for putting up with those men. 

Build a friendship getting to know her. Treat her with the respect and class any woman deserves. Then just ask her out. 

I knew a woman who had bad luck with men and seen that they "only want one thing." She was insecure and afraid to open up. But she ended up liking me because I was the opposite of everything they were like. They teased, I complimented. They rushed into things, I took it slow. They tried to get what they wanted, I showed respect and only did what she was okay with. That will get you much further. Plus, it's just the right thing to do.

[shouldhavelearned]

Like others said, less teasing and more mature conversations.

Just be open and ask her out for lunch or something one day. 

See where it goes.

[ShySoul]

Also, anyone who doesn't like someone for being too nice is just being a fool. Why wouldn't you like a nice person?

Ignore them and just focus on having a good, fun interaction with her.