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I don't know if I should ask a colleague out

Tagged as: Breaking up, Dating<< Previous question   Next question >>
Question - (31 October 2017) 9 Answers - (Newest, 9 November 2017)
A male United Kingdom age 30-35, anonymous writes:

I'm 26 and have been single for around 7--8 months now since splitting with my gf of 3 yrs. I found that break up hard and I'm unsure if I want a new relationship. However I've only been with 2 girls in my whole life and I'm desperate to "get out there" and do more, meet more people etc. but I find it difficult. I'm not the most confident person and I see everyone else having fun and loads of girls and I want some of that. But part of me is unsure. Do I want this for myself, or do I want to just put on this big front to the world of how great I'm doing but really, I don't want it?? I'm very confused a lot of the time. I have spoken to a therapist, but it doesn't seem to have helped.

I don't know if I should ask a colleague out. I have known her for around a year, and we have worked in the same team at work for around 6 months. She is very beautiful and we get on pretty well But I still don't really know her that well, and I'm not sure she even likes me back in "that" way. I have had several good opportunities to ask her out and I have a pretty good idea of what we could do/where we can go etc. for our date, but I have lost my courage each time :( should I ask her out? Even if she says no it would at least be a confidence boost for me I suppose, but I'm paranoid that if she does say no I will be the subject of jokes and gossip at work. I think I'm probably overthinking all this??! Any advice would be very much appreciated. Thanks

View related questions: at work, confidence

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A female reader, femmenoir Australia +, writes (9 November 2017):

femmenoir agony auntYou sound pretty confused to be honest, not to mention that it's only been approximately 7 to 8 mths since you and your ex of 3 years broke up.

You're hardly over that relationship and you need more time to heal, to find full closure.

You've seen a very beautiful woman at work, so whilst you're still a bit "raw" and "vulnerable" it makes sense to want to test the waters and ask her out.

It would be most likely a "failure", because it'd have been on the rebounds.

I would not advise you to ask this young lady out and because you also work together, this adds to the risks of workplace dating and the risk of things going wrong.

You should only ever pursue anybody you're attracted to, when you know that you're 100% ready and doing it for the "right" reasons and not the wrong.

Try online dating or join a social group and make new friends, before you even think about dating a new woman.

I think you should work on your head space and getting all that right first.

Get help for your insecurities and find your closure, before moving on to somebody new, because that's what "you" and "she" would deserve.

Good luck!

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A male reader, PJ Roy American Samoa +, writes (4 November 2017):

Friend,

You are not currently in an enviable state of mind. That's no excuse for not asking girls out. Forget about moping about, feeling sorry for yourself, giving yourself time to heal... those are just excuses to delay getting into Action.

Regarding your current Love Interest, who is your colleague though... I'm sorry, based on what you've written, I don't see it happening.

"I have known her for around a year,"

"I have had several good opportunities to ask her out"

"I have lost my courage each time :( "

If she had been interested, you would *know* it.

In which case, she'd have perceived those opportunities to ask her out too, which you did not capitalize on, and she'd have certainly perceived those times when you lost your courage. That would not be exactly a turn-on for her.

By now, my bet is that she has friend-zone'd you or marked it off as "nope, this one goes into the not-meant-to-be-basket... next please..."

My advice, focus on other girls outside your circle of work. Relationships with co-workers are edgy and touchy; I'm not totally against them though. So, stay tuned to how your colleague reacts to your hanging out with female acquaintances.

"Even if she says no it would at least be a confidence boost for me I suppose,"

I don't see how a rejection could be that much of a boost for your confidence. You've got this backwards. If she's just being friendly instead of strictly professional, and she has to reject you, you might be making her feel bad about her approach to professional interactions.

Be sure you've gauged the amount of risk you're prepared to accept when you do make your move.

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A male reader, TylerSage United States +, writes (2 November 2017):

TylerSage agony auntLife is short, nothing is permanent. Thinking the two of you will be doomed from the get-go is just feeding yourself with anxiety. Work on your confidence a bit, maybe you can listen/watch some motivational videos on YouTube to help. Make sure you learn more stuff about her so that you're fully prepared like "Is she open to dating a co-worker?" or "Does she have a boyfriend."

Why care if anyone makes jokes about you for asking out a gorgeous girl? You know what they say "If people aren't talking about you, you just aren't worth talking about." See the good in everything and trust that the best outcomes. If you do the easy things in life, your life will be hard, but if you do the hard things in life, your life will be easy. You're 26, live a little.

All the best.

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A female reader, mystiquek United States + , writes (1 November 2017):

mystiquek agony auntIts never a good idea to date a colleague. The relationships normally don't last and then you are stuck working with someone that you may not want to speak to, let alone see and yet you are forced to. Its hard to hide these relationships, normally other find out, the gossip starts, ect..ect.

There are too many other ladies in the world, why date someone you work with? You don't sound like you even know if you want to date, so why ask for trouble with someone you may work with for years?

Its ok to be single! I know it seems like the world is made up of couples but its truly alright to give yourself time to be alone, get to know yourself and be ready to date, not hesitant about it.

I wish you luck!

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A female reader, Anonymous 123 Italy +, writes (1 November 2017):

Anonymous 123 agony auntYoung people often get into a relationship because it just seems like the done thing. However, just because everyone else is doing it doesn't necessarily mean they're happy. You have no idea about others' lives or what goes on behind closed doors so don't ever think you're missing out.

Get into a relationship only when you are completely ready and not as an experiment.

Date someone only when you want to, not because you have to.

As for dating you're colleague, be very careful. I married my colleague but them I guess I was one of the lucky ones for whom it worked out. The others are right when they say that the workplace is not for dating because once things go wrong, it can all get really sour really quickly. It's great while it lasts but once it's over, you've had it. Also, you're not really certain about this lady and are only thinking about her because it looks like you have no other options. In this case, it will almost certainly not work out and then what's the plan? Forget being the laughing stock now, you'll be a bigger mess then.

Enjoy your alone time without thinking that the grass is greener on the other side. Trust me, it's not. It's not, it's not, it's not!! Enjoy your "single" status and do things you've always wanted to do. When the time comes, you will most certainly find the courage to ask the right girl out. Take my word for this. My husband was one of the shyest people ever and had never had a girlfriend... But he asked me to marry him within less than a month of meeting me. He didn't even have the courage or the confidence to look at girls in the eye but he asked me out almost immediately. He tells me that he has no idea how he did it but he just knew that he had to.

If he can then any man in the world can!

Don't be so diffident, enjoy life and just let go. You'll find love when the time is right :)

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A male reader, N91 United Kingdom +, writes (1 November 2017):

N91 agony auntJust from reading your question you can tell you don't really want to ask her out and you're doing it for the sake of things. What's the point in that?

I'd also strongly advise against getting involved with colleagues, like you said you could become the talk of the office, even if things went well initially but then took a turn for the worse and you had to work with each other everyday, would it be worth it?

Personally I don't think you're over your breakup, you will KNOW when you're ready to get back out there. There's no set time limit on this kind of thing but you will WANT to start looking for someone and be very pro active about it. Right now you sound like it's not what you really want. Sounds like you're forcing it.

Concentrate on getting your head straight first.

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A reader, anonymous, writes (1 November 2017):

You've pretty much answered your own question. Why bother with women you work with? When you've got to be so mindful of not crossing the wrong line; which could be misconstrued as sexual-harassment, or cause professional-awkwardness.

She would have every right to feel thrown off-guard that you think of her in any way but professional.

Women are coming to the forefront about inappropriate male-behavior on the job, and in just about every profession.

Have you not heard the news, picked-up a paper, or read the headlines on social-media?

Search-out dates and companionship through venues and websites setup for that purpose. It's better to try online-dating. Where women want to be approached for dates.

My employees begrudgingly go to mandatory sexual-harassment and workplace conduct seminars. We discourage people from using our professional office for their dating-pool. Even for offsite employee-behavior; the company holds some liability, and risk of our corporate reputability.

This huge American scandal comes out about a powerful Hollywood producer being accused by over 50 women of inappropriate behavior; to be followed-up by a firestorm of women accusing men of inappropriately approaching them on the job. Touching them inappropriately, and/or making them feel uncomfortable at work. Even sexual-assault and rape!

Companies have become too relaxed about on-the-job dating and improper conduct; and their liability for harassment suits is only going to increase. Especially in the recent climate about men assaulting and touching women!

Subscribe to a dating-site, and stay professional and courteous at work.

If she's an attractive women, she is more likely to be inappropriately approached. She has the right to feel at-ease around male employees; and not have to reject guys, and have to deal with the awkwardness and tension that usually follows.

My first few years on the job were very uncomfortable. Older women trying to set me up with dates, and younger ladies hitting on me. I'm gay. All I wanted to do was my job!

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A female reader, Honeypie United States + , writes (31 October 2017):

Honeypie agony auntHonestly, OP?

I'm very much a "don't date at work" kind of person. Because:

1. It's the place where you go to WORK, where you get your income from and where you have to have a "professional" persona.

2. If (or rather WHEN) it doesn't work out... it gets awkward, not just for YOU and her but for everyone around you.

3. The workplace should NOT be your dating pool. WHY limit yourself THAT much?

4. And then there is the possibility that she might say no. Which will make YOU feel bad, her feel bad and working together will be ... well, difficult.

Just don't mix work and dating. THAT is my advice.

If you want to go out more, socialize more then I suggest you either go out with a group of friends or coworkers. You don't HAVE to have a GF or bang a girl to have a good life.

In your spare time set yourself some goals for things, you would like to do and then DO them. They can be small goals. Maybe do sports, volunteer, find a book club, hiking group and MEET new people. Who knows who you might meet.

Asking the girl at work is YOU being lazy in pursuing a relationship that you aren't even sure you want. If you look at it a little closer.

So expand your horizon.

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A female reader, Aleisha-Jay United Kingdom +, writes (31 October 2017):

Aleisha-Jay agony auntGo for it. You will never know otherwise. No one should make fun of you for asking out someone you like and if they do, it would make them pretty immature!

In life people say no, you just dust yourself off and keep plodding :) Life is all about taking risks and if your unhappy on your own, the only person who can change that is you!

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