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!
Be direct. Ask him out to dinner specifically as more than a “social interaction”.
Be indirect. Go out for one of your social outings and then ask him near the end “So are these dates or what?”
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.
Be direct. Ask him out to dinner specifically as more than a “social interaction”.
Be indirect. Go out for one of your social outings and then ask him near the end “So are these dates or what?”
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.
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.
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.