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Asking a co-worker on a date
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Long story short. Known each other for +18 years and have worked together on projects on and off during that time.

Both divorced with grown up kids, mine very amicably his very painful 4 years ago. The past 4/5 months we have met sociably for meals drinks etc. We get on really well and all the conversations are relaxed and good fun.

He has become a really good friend and I don’t want to jeopardise that so how do I change the social get togethers into a date?

We speak regularly normally 2 or 3 times a week and often for +30 mins. We are both late middle aged and it is more than 20 years since either of us arranged a date!
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Re: Asking a co-worker on a date [Stumps] [ In reply to ]
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Three approaches:

1. Be direct. Ask him out to dinner specifically as more than a "social interaction".

2. Be indirect. Go out for one of your social outings and then ask him near the end "So are these dates or what?"

3. Be cute. Write on a napkin "Do you like me? [ ] Yes [ ]No" and pass it to him with a pen.


Other than that, if you're that comfortable with each other, maybe bring up that you have feelings for him but don't want to jeopardize your friendship, pretty much what you told us.

Level II USAT Coach | Level 3 USAC Coach | NASM-CPT
Team Zoot | Tailwind Trailblazer
I can tell you why you're sick, I just can't write you an Rx
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Re: Asking a co-worker on a date [Dr_Cupcake] [ In reply to ]
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Dr_Cupcake wrote:
Three approaches:

1. Be direct. Ask him out to dinner specifically as more than a "social interaction".

2. Be indirect. Go out for one of your social outings and then ask him near the end "So are these dates or what?"

3. Be cute. Write on a napkin "Do you like me? [ ] Yes [ ]No" and pass it to him with a pen.


Other than that, if you're that comfortable with each other, maybe bring up that you have feelings for him but don't want to jeopardize your friendship, pretty much what you told us.



I would say only #1 is a real option here. In her post, she mentioned that she is an adult and doesn’t want to jeopardize the existing relationship.
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Re: Asking a co-worker on a date [Stumps] [ In reply to ]
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If you want to change the conditions of an existing relationship, especially one with a coworker, you need to be direct. Tell him that you enjoy the time with him and your conversations and that you’d be happy to pursue a romantic relationship with him. Or something a bit nicer, being romantic is not my strong suit ;) but if he says no, it might be weird for a few days but then it should go back to normal and you can move on. Don’t play games, he’s your coworker and you’re friends, you don’t want to mess with that.
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Re: Asking a co-worker on a date [Dr_Cupcake] [ In reply to ]
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Well the answer would appear to be non of the above!

We went for drinks with another co-worker last week-end and just kissed at the end of the evening and now we are dating.

He isn't into triathlon though which is good because we aren't the type of people who will do everything together.
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Re: Asking a co-worker on a date [Stumps] [ In reply to ]
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Go Stumps!!!

Formerly GiantNewb, but not such a newb anymore.
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Re: Asking a co-worker on a date [Stumps] [ In reply to ]
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Haha that works too! Way to go!

Level II USAT Coach | Level 3 USAC Coach | NASM-CPT
Team Zoot | Tailwind Trailblazer
I can tell you why you're sick, I just can't write you an Rx
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Re: Asking a co-worker on a date [Stumps] [ In reply to ]
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YAY!!!

I'm glad it turned out well. Have fun!
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Re: Asking a co-worker on a date [edbikebabe] [ In reply to ]
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I’m so glad for the update an that it went well! Good luck!
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