Asking for a nervous friend - male and wants to crowdsource perspective. He has struck up a friendship with a woman at work (lets call her Alice) and he likes her. They meet in passing most days in the lunchroom. They chat and share a sense of humour. They work for the same company but different divisions. He wants to ask her out but is nervous and is scared about being icky. He has never asked anyone out before. If he was to ask a mutual friend of his and Alice who works with Alice (lets call her Mary) out for a drink on Friday night - which is a totally normal platonic thing - as he and Mary often will have a beer on Friday after work. Then - if he were to mention to Alice in passing that he and Mary were planning on going for beers and would wonder if Alice would like to join them - and if Alice agreed, do you think Alice would be wise to a deeper plot? I believe he's hoping that she would be.
My partner's 18 year old sister wants to marry her boyfriend of one year. They both live at home with their respective parents, are not planning to pursue post-secondary school, and are financially insecure (she does not work, he works part time). They have recently converted to a fundamentalist version of a new faith, and their plan is to rely on her disabled mother who would lose her benefits by caring for them - the mother is against this but of course loves her daughter. Their religious community is encouraging them (but not offering financial aid). What can we do to support her but not her decision? [more inside]
What more do I need to say to a friend who I'm sure is headed for a fall? [more inside]
What immigration/visa options are there for an American girlfriend and Canadian boyfriend? [more inside]
Please help my wife identify a music video from the eighties. [more inside]
HelpMeGiveGoodAdviceFilter: My very early-20s friend is in a long-term relationship approaching two years. They love each other, they love each other a lot, but he's restless for the "hunt" among other issues. I'm torn between telling him settling down is inevitable in any LTR and cautioning him not to commit himself too early before he's gotten his play out of his system. There's much [more inside]