Help required for approaching a crush after awkward scenario [closed]

Question

I'm 25 and have a huge crush on this girl who is 29. We were working in the same office and were casual friends. I guess she also likes me as I noticed her staring me several times. Also, she was the first to initiate the conversation most of the times when we met in the office (I am a bit of shy & introvert type). Also, when once we were passing by each other through the office corridor, I just walked straight without making an eye contact with her because of my nervousness, she followed me couple of steps and asked me why just I passed by without greeting or saying anything.

So, because of these reasons I felt there are chances she also likes me. So, once I casually asked her reason for staring, she got tensed and said there is nothing like that and I'm like her younger brother. But I think, she said this in stress because she might have thought I was complaining and I'm younger than her. But I'm not sure about this. Because she asked if there is any gossip of her staring me in the office. She seemed very much worried about that. But there was really nothing like that. I told her. But she did not seemed convinced and I feel she believed about the gossip which never happened. I’m from India and most of the people here are not open minded about such things. They consider the people in love, relationship as spoiled and mock at them. So, because of this, I understand her tension if she believed about the gossip.

I think the question about staring have freaked her out. I agree that was a damn stupid approach. I regret that. But I had no intention of hurting her and was expecting a positive response from her on that question. I have said sorry to her if I have hurt her and told her that I was just kidding, and she said it is OK and have forgotten about that. But still she seemed tensed to me.

She had left our work place around two months ago (for better job opportunities) only making my chances to approach her difficult as hell. Her memories haunts me every single day since she left. She doesn’t have profile on any social media either. She can be contacted only through phone. I have got her phone number from her friend after she left. But contacting her on phone seems somewhat awkward to me because of the weird scenario happened and the fact that I did not got her phone number directly from her.

My dad works as life insurance adviser and sells life insurance policies, so on her last day I asked her whether she has any requirement of life insurance. She said she had not decided about insurance that time. Now I am planning to text her if she has decided anything on insurance. Will this be a right approach? If she says yes to that I will have chance to meet her at least one time on that purpose. But what if, if she says no to that? How do I initiate conversation/message on phone that will not make her awkward if possible? This time I want to keep communication as natural as possible and do want to sound desperate and not scare or hurt her anymore. Any advice on this?

If she is not having the same feelings as me, I at least want to be friend with her for a long time, for always.

Answer 1

Now I am planning to text her if she has decided anything on insurance. Will this be a right approach?

That's......... creative. You're overthinking this. Why not try something simple instead?

"Hey, I'm Steve from work, what are you up to?" or "wanna catch up" or meet up or whatever.

If she wants to talk to you, what you say doesn't really matter that much, as long as you don't shoot yourself in the foot by crafting an elaborate plan like your insurance thing, you're not crafting a trap to catch a mythical and elusive fairytale beast, just tell her you want to have some coffee, goddammit.

If she isn't interested in talking to you, what you say doesn't really matter, either she won't reply or she'll say no, and that's it.

Now, have a look here and read Tinkeringbell's answer, which is a wonderful opportunity to remember that just because a woman was nice to you, doesn't mean she wants to get into your pants. Maybe she was just being nice? Don't let that stop you from asking her out if she gives signs of attraction, but please don't write a three-page love poem just because she bumped into you in the corridor.

Don't put pressure on her (as in, imply you'll be very sad if she says no) or raise the stakes (by reserving in an expensive restaurant before you know she's interested) and don't say stuff that makes you sound obsessed like "I've been thinking about you non-stop for two months" in the first message! Save these for the third date or something. Opening the conversation with that would be a bit..... creepy.

There's nothing wrong with "what are you up to, wanna catch up and have a drink?"

Now I wanted to show an example of what not to do, but the image apparently offended some sensitivities. If you want to see how NiceGuy Brad from reddit (where else!) gets rejected, check the previous revision of this post, and do the opposite. ie, if she says no, reply "okay, bye!", and definitely not a two-page rant about how unfair life is (and it's all her fault).

Answer 2

I am going to refer you to a couple other questions you should read that relate to your question.

Gift giving avoidance when individual has been avoiding me

And

How to contact a girl whose number I got from somebody else?

Any advice on this? What can be her true feelings or how can I know about them?

Seems to be your questions are framed in how do I approach her, and some scheme about asking her about life insurance. Your way over thinking here, it is what us shy introverted people do because we fear a negative outcome. Which keeps us from getting to the occasional positive result.

My advice here is move forward and do not worry about the outcome. Make that call and ask her out, don't make any excuses for the call just give her the honest reason for the call. You have missed her since she left work and would like to take her out. (note: there is no life insurance in that statement of intent)

Simply bite the bullet with your fears and move forward and handle the outcome when the outcome becomes real instead of products of fantasy and fear. Move forward and these problems you have posted about will not be problems.

What her true feelings are you will have no way of knowing until you make the call. Rather your rejected totally, end up with a friend or a significant other, you just cant know until you fulfill a little destiny, and you cant fulfill destiny until you move forward.

Answer 3

Staring at someone is a common thing but asking the person about it would be a confrontation and undoubtedly, your crush felt real awkward about it. You regret it but she doesn't see it that way.

Unless you take a step forward, you wouldn't know how she feels about you. Do not talk about that insurance thing, ever. If she wants one, she'll approach you.

Just call her up, but do not talk about those awkward moments or insurance thing. Tell her that, if given a chance, you would like to start it over again. If you are not comfortable saying it, just say that you want to meet over a cup of coffee.

Remember, being confident is the key here. Be prepared for the outcomes and have a clarity about how you want to talk to her. Rehearse, a lot.