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I’m tempted to ask her out but fear embarrassing her!

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Question - (14 April 2018) 7 Answers - (Newest, 16 April 2018)
A male United Kingdom age 30-35, anonymous writes:

There is a girl at my work that I have liked for years, but I never had the courage to talk to her until recently, after she asked a colleague who I was and was I single. We get on quite well but there is a little bit of shy / awkwardness when we chat. She knows I like her, and I know she likes me, but when a mutual friend asked her for her number for me, she panicked, said she’d think about it, and walked off, and I’m not sure why.

Our mutual friend seems to think she has never had a boyfriend, and suspects she may be a little inexperienced, maybe even a virgin. This is not an issue for me and I’d be fully prepared to take things slow, but bearing this in mind, I’m scared to ask her out incase she panics again and the whole friendship is ruined.

Any advice on how I can approach this? I’m often tempted to ask her out or for her number but the fear of embarrassing her always puts me off!

View related questions: never had a boyfriend, shy

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A male reader, anonymous, writes (16 April 2018):

FGS you are 30 yrs old and you are too shy to talk with a chick and ask her for a date? Don't be shy. Ask her! The worste possible thing that can happen is that she will say no. She is not going to eat you. And I advice you to keep sex out of your mind for the time being. Maybe those thoughts are making you embarressed to talk to her. Good luck bro.

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A female reader, Dionee' South Africa +, writes (15 April 2018):

Dionee' agony auntThere is no real friendship there so don't be fooled.

I always say that dating people at work can open a can of worms that nobody will be prepared for. In my opinion, I think especially if she seems inexperienced; leave her alone. Because of the fact, things may not work out and she may be attached and extremely heart sore should they not work out... then what? you've created a hostile working environment at work and someone may have to leave the company.

Judging from her reaction, she may have felt cornered. It was like poking a bear with a stick. Also, why is your friend asking for numbers for you? I honestly thought it was someone really young posting this after reading this in it's entirety and then I realised it's a grown man posting this... which is weird.

I say, in future, don't team up on girls and also, stay away from going after girls that you work with unless you're absolutely sure that you plan on marrying them, building a family and dying in each others arms in your old age (I don't think anyone is that sure). In essence, steer clear.

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A female reader, Aunty BimBim Australia + , writes (15 April 2018):

Aunty BimBim agony auntYou are a grown up, in your 30s, why in heaven's name did you need to involve a third party here, like a bloody school kid, to ask for her number on your behalf??

Who cares what your mutual friend thinks about her sex life or previous relationships.

The girl could very well be thinking the two of you are talking about her and ganging up on her ... its possible she doesn't like the thought of being discussed like next weeks roast lamb.

There could be some concern that IF she did happen to go out with you the date would then be discussed by you and the "mutual friend" ...

If you MUST ask her out, do it yourself and don't involve third parties, and make it something simple, like a coffee out of work hours. Develop some decorum and keep the meddling mutual friend out of it.

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A female reader, Honeypie United States + , writes (15 April 2018):

Honeypie agony aunt

Normally I'd advice against looking to date coworkers. 1. If she isn't interested it might feel VERY awkward for her to have you ask.

If it just doesn't work, it might be awkward for BOTH of you and awkward for the coworkers too.

So, I generally think dating or trying to date coworkers is a "bad" choice.

BUt if you are going to do it regardless...

Ask her out for coffee after work, she can pick the day sort of thing. something that doesn't SEEM like a date - date. That way you can see if you two actually CAN carry on a conversation.

Now if she tells you, I'll get back to you... TAKE it as a NO, thanks. OK? RESPECT that.

Instead of asking her for your number you could give her yours.

If she panics this much about someone asking for her number... do you really think she is at a stage in her life where she is ready to date? She doesn't sound like she is looking to date ANYONE.

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A male reader, WiseOwlE United States + , writes (15 April 2018):


"You and your friend are taking advantage of her inexperience and you are both way out of line. Lucky I'm not your boss! She thinks you're a couple of lecherous creeps; and you've both embarrassed her. Apparently he is not a "friend" as far as she's concerned. I know exactly why she walked off!"

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A male reader, WiseOwlE United States + , writes (15 April 2018):

Your "mutual friend" also stepped across a line close to what is considered sexual-harassment and creating a hostile work environment for women. Maybe in the UK you can corner women and ask for numbers; because they can't run from you, or you can place them on the spot. It better not happen here in the States!

Why? Because women say they're sick and tired of it!

You and your friend are taking advantage of her inexperience and you are both way out of line. Lucky I'm not your boss! She thinks you'r a couple of lecherous creeps; and you've both embarrassed her. Apparently he is not a "friend" as far as she's concerned. I know what she walked off!

Hang-back, dude! This is where you earn your paycheck. You better practice professionalism and leave women alone where you work. I would advise her to report you and your flirtatious friend to Human Resources.

Keep your presumptions and speculations about her virginity to yourselves.

Back-off, Jack! I think you're both asking for trouble, and you're harassing that poor young woman!

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A female reader, anonymous, writes (14 April 2018):

What friendship .. your casual acquaintances at work .. You know nothing about her other than you like her .. I mean there no depth to what you put so where the friendship . Plus saying at work never works out and become more awkward then to start with

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