Mr D asks:
You could always start off with "Do you want to go out with me?" or "Would you go out with me?" or depending on the situation and your ego "Do you want to be my girlfriend" or "Can I be your boyfriend". Some possibilities. It really is kind of limitless in how you go about it.
The situation deepens however because their history is kind of spotty. The last time they thought things were going well with a girl, and then they asked them out to date, it went avocado shaped (pear shaped but bumpier) and horribly wrong. They had no idea why it turned out that way when they had been hanging out fine, having gone to movies, had conversations, meals etc, even with him using her shoulder and lap as a pillow before. Of course, some people, both guys and girls, are quite capable of being very platonically affectionate, but once you throw in romantic ideas and attachments, zoom, they're off into the distance.
So, his object of attention, Miss E, has been so far apparently fine with the hanging out, conversations and so forth, but he isn't sure if the timing is correct, or what the true outcome will be. My advice to him was, give her the option. Try using something like this:
"I'd like to go out with you, perhaps be your boyfriend, but I understand if it's too soon, or a bit quick, so if you like we can continue to hang out like before until you decide on what you would like to answer". It's simple-ish, humble (instead of saying them being yours, you be theirs), gives them the opportunity to wiggle away if they find the situation awkward, but at the same time gives them breathing space for nothing to change immediately but the purpose of your pursuit is made clear.
In any case, with Mr D, I think I will probably end up hearing about how it goes at some stage since he often asks me these things, such as went things with Miss F went horribly wrong last time.
I've been hanging around with her a lot lately, but how do you ask someone to go out with you? I'm not sure if it is the right time to ask.
You could always start off with "Do you want to go out with me?" or "Would you go out with me?" or depending on the situation and your ego "Do you want to be my girlfriend" or "Can I be your boyfriend". Some possibilities. It really is kind of limitless in how you go about it.
The situation deepens however because their history is kind of spotty. The last time they thought things were going well with a girl, and then they asked them out to date, it went avocado shaped (pear shaped but bumpier) and horribly wrong. They had no idea why it turned out that way when they had been hanging out fine, having gone to movies, had conversations, meals etc, even with him using her shoulder and lap as a pillow before. Of course, some people, both guys and girls, are quite capable of being very platonically affectionate, but once you throw in romantic ideas and attachments, zoom, they're off into the distance.
So, his object of attention, Miss E, has been so far apparently fine with the hanging out, conversations and so forth, but he isn't sure if the timing is correct, or what the true outcome will be. My advice to him was, give her the option. Try using something like this:
"I'd like to go out with you, perhaps be your boyfriend, but I understand if it's too soon, or a bit quick, so if you like we can continue to hang out like before until you decide on what you would like to answer". It's simple-ish, humble (instead of saying them being yours, you be theirs), gives them the opportunity to wiggle away if they find the situation awkward, but at the same time gives them breathing space for nothing to change immediately but the purpose of your pursuit is made clear.
In any case, with Mr D, I think I will probably end up hearing about how it goes at some stage since he often asks me these things, such as went things with Miss F went horribly wrong last time.
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