Does it have to be a one-on-one thing? Does it have to be direct ("Do you want to go out with me on Friday night?" or something)? A couple of days ago his guy asked me if I wanted to hit the beach with him. He asked really casually over messenger though I started the conversation (I thanked him for helping me out a bit with something the day before & then he said it was no prob & asked about going to the beach). He said it'd be fun but unfortunately I had work to do so I had to decline.
I asked who else was going & he said a few his friends whom I didn't really know too well. Is this a form of "asking out" or does it mean nothing at all? Also, if a girl declines once or twice (even with a valid-sounding reason), will this discourage a guy to ask again (even if it's really casual)?
I think "asking out" is a one-on-one thing with clear romantic intentions, whereas asking you to join him and his friends at the beach would be more like "hanging out." Still, it could be a good sign that he wants to get to know you better so that maybe he can ask you out for real in the future.
As long as you make it clear to him that you would have liked to have gone with him but you had prior engagements, he may not be discouraged. If you're interested in this guy, then continue being friendly to him and chatting with him over IM, text, etc.
Well by the sounds of it it isn't strictly a date, but it sounds like he is keen on your company. Guys are shy about making moves with girls too you know, so it would be a pretty safe way to invite you to hang out more. I think someone would understand a , ' I can't come I have work' but if your particularly concerned about discouraging him you can always also say something like 'hey sorry, I have work , but I'd be up for it some other time'.
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