Should I just ask him on a date?

If you do something just to please her despite knowing it will be difficult, you are introducing an element of potential unhappiness in your relationship. Healthy relationships are about honesty and openness

I want to try and get closer to a friend of mine, to see if we are compatible and gauge how he really feels about me. I sometimes get a sense that he likes me and wants to move beyond a casual friendship, but he doesn’t say anything specific which makes it hard for me to judge what’s going on in his mind. I can’t ask him a direct question either because that may lead to some unnecessary drama if I have misread the whole vibe between us. Some of our common friends know there is this interest between us, but they haven’t said anything to me either, making me sometimes wonder if this is all in my mind. I can’t even ask him out on a date because we only meet as a group. What do I do?
Nothing stops you from reaching out to him away from your group via your phone. Nothing stops you from asking him out for a cup of coffee because not meeting individuals isn’t a rule set in stone. The easiest way to avoid misunderstanding a person or situation is to ask questions, or have more conversations, because speculating in silence always leaves room for error. If he agrees to meet you, it’s a sign. If he refuses, that is a sign too. Why overthink it?

My girlfriend recently asked me to consider going on holiday with her but wants to bring her siblings along, too. I find this strange because I don’t know them well and won’t be comfortable around them. She thinks it’s normal and I don’t know what to tell her.
If something makes you uncomfortable, you have a right to avoid it. If you do something just to please her despite knowing it will be difficult, you are introducing an element of potential unhappiness in your relationship. Healthy relationships are about honesty and openness. 

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