How bad an idea is this.

[ZA Dater]

My own judgement says there is little upside to this idea but maybe I am wrong about this.

Basically is it always a bad idea to date in the business world? For example the scenario here is a lady who works at one of my clients, hard to judge age, no wedding ring, definitely I would term her as attractive, Australian (for some reason I like accents) and I am wondering should I try and suggest a coffee and see.

What puts me off the idea

1: Close working relationship sort of in that I see her once a week

2: The fact that even the business conversations I have had with her are awkward and really do not flow 

3: I am not picking up any positive body language.

4: I already know I am terrible to date and am not really "fun".

Its just do not see someone like her being very receptive to someone awkward like me. One of the great mysteries of life to me is how some guys/many guys just have the confidence to try this without considering the outcome. 

I also ask myself what I am hoping to accomplish and that is a much more difficult question, perhaps just share life I suppose, I am still feeling quite damaged to be honest after being dumped, just poured every ounce of energy into work to try and forget.

[Foxhall]

13 minutes ago, ZA Dater said:

One of the great mysteries of life to me is how some guys/many guys just have the confidence to try this without considering the outcome. 

a novelty for me to be the first responder!

Personally when had a bit more success with women in recent time- early 40s probably / definitely considered a late developer,

I suppose I am not as bothered now as to what they think of me- I have found that many women are milder and easier to talk too that I had for a long time previously feared,

so be more confident and less hesitant about approaching in general,

that being said in terms of this particular approach, you would be better I imagine to build up stronger rapport in a business context initially, before chancing your arm otherwise,

 

 

Edited February 21, 2023 by Foxhall

[ZA Dater]

4 minutes ago, Foxhall said:

a novelty for me to be the first responder!

Personally when had a bit more success with women in recent time- early 40s probably / definitely considered a late developer,

I suppose I am not as bothered now as to what they think of me- I have found that many women are milder and easier to talk too that I had for a long time previously feared,

so be more confident and less hesitant about approaching in general,

that being said in terms of this particular approach, you would be better I imagine to build up better rapport in a business context initially, before chancing your arm otherwise

 

This was my thinking to some extent but might be a challenge considering how awkward the conversations generally are and the fact I'd be very surprised if she is single.

Suppose I could change up the conversation a bit and perhaps be less businesslike.

Edited February 21, 2023 by ZA Dater

[Foxhall]

Maybe yes,

I am thinking of an attractive friend I have and she would say she likes a man to show confidence and take that step to approach her and so on,

then again the initial conversations with someone- you tend to sense or not whether there will be rapport with the person,

If its quite awkward   chances are she is not for you, any women that I get on well with -the first conversations were positive,

I dont see anything wrong with trying your luck in the business environment generally, but am guessing you will be better served by meeting a slightly more outwardly friendly lady,

this one will need a bit of breaking down

 

[glows]

This is really at your discretion. Some are automatically turned off at the idea of dating in the workplace. Nothing to do with you.

Others are more open to the idea. If conversation isn’t flowing and she doesn’t seem interested in holding a conversation with you, then don’t push it at the risk of appearing unprofessional and inappropriate. The workplace generally isn’t a club or dating app. 

[ZA Dater]

49 minutes ago, glows said:

This is really at your discretion. Some are automatically turned off at the idea of dating in the workplace. Nothing to do with you.

Others are more open to the idea. If conversation isn’t flowing and she doesn’t seem interested in holding a conversation with you, then don’t push it at the risk of appearing unprofessional and inappropriate. The workplace generally isn’t a club or dating app. 

Yea I am leaning towards this maybe just enjoy any sort of interaction, even when the conversation does not flow. Anyone here ever battle with this?

Irony is the workplace is where most people spend most of their time. 

I guess here I simply like the looks abs accent hence considering something I probably should not. Which I guess is superficial but I readily admit I am that.

 

[ZA Dater]

1 hour ago, Foxhall said:

Maybe yes,

I am thinking of an attractive friend I have and she would say she likes a man to show confidence and take that step to approach her and so on,

then again the initial conversations with someone- you tend to sense or not whether there will be rapport with the person,

If its quite awkward   chances are she is not for you, any women that I get on well with -the first conversations were positive,

I dont see anything wrong with trying your luck in the business environment generally, but am guessing you will be better served by meeting a slightly more outwardly friendly lady,

this one will need a bit of breaking down

 

Good advice, I did something the other day and noted how my conversations go, there are generally no frills so I guess some people think I an abrupt. 

Haha yeah have to honest few of my conversations with ladies are initially positive, more like this scenario I try understand the situation and level of risk versus what I can ultimately accomplish.

 

[glows]

15 minutes ago, ZA Dater said:

Yea I am leaning towards this maybe just enjoy any sort of interaction, even when the conversation does not flow. Anyone here ever battle with this?

Irony is the workplace is where most people spend most of their time. 

I guess here I simply like the looks abs accent hence considering something I probably should not. Which I guess is superficial but I readily admit I am that.

 

That’s fine - nothing wrong with chit chat. It makes working much more pleasant when we have that mutual understanding and can get along with everyone. Keep those interactions positive in light that it is someone’s workspace even if you feel more at ease. The point is it’s a two way street: ok if you like it, be sure you’re not making someone else uncomfortable.

I got a call from someone with a strong southern accent. I was smiling while on the phone not realizing at the time. A colleague commented. Speaking of accents.

 

[Johnjohnson2017]

"2: The fact that even the business conversations I have had with her are awkward and really do not flow"

I agree with the above posters. #2 is the most important clue. If it is an awkward conversation, don't even think about asking her out. Wait a couple of months to see if the vibe is better, then reassess. Right now it is a red light.

[Alpacalia]

It's always a good idea to be cautious when considering dating someone in the business world, especially if you work with them closely. It's important to weigh the potential risks and consequences before making a decision.

I haven't dated in the workplace but I know of couples that have met through work and it worked out fine.

In your case, it sounds like there are several factors that are making you hesitate, such as your working relationship, the awkwardness of your conversations, and the lack of positive body language. If you don't feel confident that there is mutual interest, it may be best to avoid making a move.

It's also worth considering your own motivations for wanting to ask her out. If you're still feeling hurt and damaged from being dumped, it may be best to focus on healing and rebuilding your confidence before pursuing a relationship.

Ultimately, the decision to ask her out is up to you, but it's important to be aware of the potential risks and to make sure that you're considering all of the factors involved.

[ZA Dater]

1 hour ago, Alpacalia said:

It's always a good idea to be cautious when considering dating someone in the business world, especially if you work with them closely. It's important to weigh the potential risks and consequences before making a decision.

I haven't dated in the workplace but I know of couples that have met through work and it worked out fine.

In your case, it sounds like there are several factors that are making you hesitate, such as your working relationship, the awkwardness of your conversations, and the lack of positive body language. If you don't feel confident that there is mutual interest, it may be best to avoid making a move.

It's also worth considering your own motivations for wanting to ask her out. If you're still feeling hurt and damaged from being dumped, it may be best to focus on healing and rebuilding your confidence before pursuing a relationship.

Ultimately, the decision to ask her out is up to you, but it's important to be aware of the potential risks and to make sure that you're considering all of the factors involved.

Thanks for this, this is really very insightful. Yeah you are right I need to understand the why and part of it is me just being very lonely and wanting some attention, when I think about it now both of those are has reasons. 

Lot of what I do each day is assess risk versus reward.

Healing is proving very difficult, confidence was always pretty low but yea I think to think more about the why.

[smackie9]

I feel you need to stop putting them up on a pedestal, making you think they are out of reach. That's what is making it awkward. It pushes your confidence level down. I know it's hard but changing your perspective about someone would really help over come this sort of thing. 

[Alpacalia]

53 minutes ago, ZA Dater said:

Thanks for this, this is really very insightful. Yeah you are right I need to understand the why and part of it is me just being very lonely and wanting some attention, when I think about it now both of those are has reasons. 

Lot of what I do each day is assess risk versus reward.

Healing is proving very difficult, confidence was always pretty low but yea I think to think more about the why.

Welcome! I would like to ask, if I may, where does all this low self-confidence come from?

[ZA Dater]

1 hour ago, smackie9 said:

I feel you need to stop putting them up on a pedestal, making you think they are out of reach. That's what is making it awkward. It pushes your confidence level down. I know it's hard but changing your perspective about someone would really help over come this sort of thing. 

You are absolutely right! Its exactly this which makes every interaction like this  much more difficult. I have asked myself why I do it and the conclusion is because my general experience at trying to chat to people like this is generally very poor so I am starting off from a base of being inferior, its hard to type that but its the truth. In the context of life I try to make someones day better each everyday and again it comes from the point of view that so many people judge me, nasty comments are passed and yes they should not stick but they do. 

To give you and idea conversations with this person are so awkward, I try to not make them awkward but it inevitable turns out that way, to counter this I try give back something in the form of being helpful, its my default, if the conversation goes badly I thrown kindness at it which is not to say I am not kind. 

Equally though the above can also go to far when people are nice to me I see more to it than there actually is which sets me up for a big bump down to earth. Thanks for you post though it made me think about this more than I have recently.

[ZA Dater]

40 minutes ago, Alpacalia said:

Welcome! I would like to ask, if I may, where does all this low self-confidence come from?

Perpetual failure and dating and the one time did I actually succeed I contrived to mess things up so badly there is no going back. My problem with this sort of approach is a lack of belief too, my thought process runs that anyone attractive to me is not single, sadly this has proven to be true more often than not. 

There has been some great advice here, what I think might be best is to just keep the conversations business like and park the idea of asking her for coffee. I was actually considering sending roses but to be honest I ran out of time and the three times I did that in life the gesture was unappreciated I never even got a thank you so I am loath to ever do that again.

[Alpacalia]

20 minutes ago, ZA Dater said:

Perpetual failure and dating and the one time did I actually succeed I contrived to mess things up so badly there is no going back. My problem with this sort of approach is a lack of belief too, my thought process runs that anyone attractive to me is not single, sadly this has proven to be true more often than not. 

There has been some great advice here, what I think might be best is to just keep the conversations business like and park the idea of asking her for coffee. I was actually considering sending roses but to be honest I ran out of time and the three times I did that in life the gesture was unappreciated I never even got a thank you so I am loath to ever do that again.

Thank you for sharing your thoughts with me.

Negative thought patterns and limiting beliefs may hinder potential connections, so it's important to challenge them. The belief that attractive people are not single is an example of a limiting belief that can prevent you from exploring potential relationships. Consider evidence to the contrary, such as knowing attractive singles or people who have found meaningful relationships despite initial challenges.

In regards to your decision to keep conversations business-like and park the idea of asking her out for coffee, you need to understand why you are considering this.

That's why I asked earlier what you felt were your motivations for doing so.

That's okay if you aren't interested in pursuing a romantic relationship. In spite of this, if you're afraid of rejection, it might be worth exploring further. Over time, small steps like asking questions and showing interest in their hobbies can help build a connection.

Flowers can be thoughtful, but may not always be appropriate. With time and effort, you may find that meaningful connections can be built without relying on grand gestures or preconceived notions of what a successful date or relationship should look like.

Edited February 21, 2023 by Alpacalia

[Lotsgoingon]

I recommend you approach people that you have had really good interactions with--or at least not bad reactions.

That way you're building on what's already there. And it's less of a leap, which can lower people's anxiety. 

Besides her looks, is there something you really like about her when you have observed her in action or talked to her? I mean, if you can have tense conversations with someone and yet love their voice and the way they think and in that situation, I say OK, approach the person.

I recommend against approaching based on looks alone--unless you are really really confident. Approach based on energy and vibe and good exchanges. 

 

[basil67]

7 hours ago, ZA Dater said:

2: The fact that even the business conversations I have had with her are awkward and really do not flow 

3: I am not picking up any positive body language.

Based on this, asking her out is a bad idea.  The ease in which we talk to somebody prior to asking them out is the clue as to whether or not they are likely to accept.   And for the life of me, I can't understand why you'd ask someone out if the conversation doesn't flow.  It would make for horrible dates for both of you.  

Further, in the unlikely even that she did say Yes, what have you learned from your last relationship and how would you do things differently?  Specifically thinking about being a warm lover and being happy to stay overnight at her house.  You've got to get this sorted out before thinking about dating again or else the relationships will end the same way as the previous one.

[ZA Dater]

8 hours ago, basil67 said:

Based on this, asking her out is a bad idea.  The ease in which we talk to somebody prior to asking them out is the clue as to whether or not they are likely to accept.   And for the life of me, I can't understand why you'd ask someone out if the conversation doesn't flow.  It would make for horrible dates for both of you.  

Further, in the unlikely even that she did say Yes, what have you learned from your last relationship and how would you do things differently?  Specifically thinking about being a warm lover and being happy to stay overnight at her house.  You've got to get this sorted out before thinking about dating again or else the relationships will end the same way as the previous one.

I did think about this but was not 100% sure, thanks for confirming my thinking. In the past almost every date I have been on has been a exercise in trying to get conversation to flow so it a near constant challenge.

After my last experience I am even less likely to want to do this, so its a catch 22 on many levels. 

What I was thinking with asking her our was to try find some sort of company but at least looking at the replies here this seems like something which will not work on any level. I also know I will not find what I had ever again so asking someone else out was a sort of band aid on a gaping wound. 

[ZA Dater]

9 hours ago, Lotsgoingon said:

I recommend you approach people that you have had really good interactions with--or at least not bad reactions.

That way you're building on what's already there. And it's less of a leap, which can lower people's anxiety. 

Besides her looks, is there something you really like about her when you have observed her in action or talked to her? I mean, if you can have tense conversations with someone and yet love their voice and the way they think and in that situation, I say OK, approach the person.

I recommend against approaching based on looks alone--unless you are really really confident. Approach based on energy and vibe and good exchanges. 

 

Good advice, the vibe thing and energy  I simply do not understand. Good exchanges, again for someone like me a good exchange could be something other see a just friendly. The problem I have is every single interaction I have most days with people is business so I treat them as such, there is the absolute bare minimum of small talk, I get to the point quickly and that is how the conversation goes. I am trying to add in more small talk but its a challenge.

[ZA Dater]

10 hours ago, Alpacalia said:

Thank you for sharing your thoughts with me.

Negative thought patterns and limiting beliefs may hinder potential connections, so it's important to challenge them. The belief that attractive people are not single is an example of a limiting belief that can prevent you from exploring potential relationships. Consider evidence to the contrary, such as knowing attractive singles or people who have found meaningful relationships despite initial challenges.

In regards to your decision to keep conversations business-like and park the idea of asking her out for coffee, you need to understand why you are considering this.

That's why I asked earlier what you felt were your motivations for doing so.

That's okay if you aren't interested in pursuing a romantic relationship. In spite of this, if you're afraid of rejection, it might be worth exploring further. Over time, small steps like asking questions and showing interest in their hobbies can help build a connection.

Flowers can be thoughtful, but may not always be appropriate. With time and effort, you may find that meaningful connections can be built without relying on grand gestures or preconceived notions of what a successful date or relationship should look like.

Agreed and its a constant struggle to challenge them. Sadly I know no attractive singles and when I did it was quite telling who they partnered up with and this unfortunately just reinforced my thought patterns which is why when I saw this lady I thought, "this is unlikely go well" and yet.....

I agree with meaningful connections, for me just about the only asset I have is kindness so that is my go to trait to and build connections but this is probably more useful with being friend zoned (I am not against this but practically it does not work).

I'll be quite upfront I am superficial so when I see her around its looks and accent I find attractive, I'll be slammed for admitting this but I am being honest, most of this is because the notion I am rejected on looks (among many other things). 

My judgement is very off most of the time and in a social setting I just get completely overshadowed by anyone else who is there so part of me thinks these sort of "work" settings might work a bit better but there are lots of pitfalls associated with this, most cannot be mitigated completely.

Why I was considering this is because well its not like I have any other options. Thanks to the members here I will park this idea indefinitely, it was a stupid idea and thanks for correcting my thinking.

[Foxhall]

Going off the topic slightly but I thought this might be a useful anecdote,

so there is this very pretty girl I know (I wont get into how I met her)- she owes me a favour or two as the saying goes

 I mention two different guys- two decent guys- looking for women and could she do anything for me or for them more specifically.(hook them up with friends etc)

Guy A- great personality, talker , puts people at ease straight away. had loads of girls when  in his 20s. Problem for him is he lost his way workwise, and now is living with his parents in his 40s , no ambition, no house, car. money ,women,  struggling with all those areas

Guy B- Has the things that the other guy doesnt have- good job, money, big house, car and so on. His problem is he is extremely quiet and shy. Even for me trying to make conversation with him is hard work. Anyway hes a lonely guy and missing out on the joys of what a woman could bring him.

so my friend the lady, when I proposed these two gents to her, she said Guy A was an absolute No No, that the ladies want to see some level of success and ambition and that was more important than personality,

Guy B she would be prepared to find a date for, fair enough he will need to work on his personality and overcome his shyness, but this guy would still be deemed a good catch.

It strikes me all your threads that your worry is that your personality is not bright enough or whatever, but if you have success and ambition and are holding down a job and so on, you still have a decent chance.

 

 

 

 

 

[Wiseman2]

21 hours ago, ZA Dater said:

 a lady who works at one of my clients

It's great you're noticing what type of women you're attracted to. However because she's a client's employee, this is not a good situation to pursue.

[BaileyB]

23 hours ago, ZA Dater said:

2: The fact that even the business conversations I have had with her are awkward and really do not flow 

3: I am not picking up any positive body language.

Based on this, I would also say it’s a bad idea. For someone to want to date you, there needs to more than the fact that you find her attractive and you think her accent is cute. If she is not giving you any signals that she is interested, things are just going to get more awkward if you ask her out. 

[ZA Dater]

10 minutes ago, BaileyB said:

Based on this, I would also say it’s a bad idea. For someone to want to date you, there needs to more than the fact that you find her attractive and you think her accent is cute. If she is not giving you any signals that she is interested, things are just going to get more awkward if you ask her out. 

Yeah, I will park this idea, it was a moment where I forgot pure logic. Honestly yesterday someone smiled at me at a restaurant which I just took at face value, that is my problem interest is not something I really notice and I fall into the trap of aspirational dating which I suppose is by product of working for 11 hours a day and then thinking of work for most of the other waking hours. 

Agee it would be very awkward so I wont do anything, it would just make any dealings going forward very challenging and I have enough on my plate at the moment.