I’m 21, he’s 20; after four months of dating, we started having arguments and misunderstandings. He’s raised trust issues. I believe it’s because he’s had multiple friends-with-benefits, and been quite the player. I’m his first love and he is scared of getting hurt.
If my phone rings, he asks who’s calling; he’s gone through my email and Facebook account. I have insecurities too, but not like his.
I’m in college and suggested we see each other only once a week. He was upset.
I’m wondering if this will work long-term because of his jealousy. I don’t see myself with him for too long.
I thought about time off and the idea of not being with him isn’t as bad as I’d anticipated!

- Confused

Follow your instincts here and end it. There’s no confusion – he’s transferred his own past behaviour to an image of you being a player. And his checking up on you is just the beginning of a routine of being questioned, having your privacy invaded, always being monitored and frequently suspected.
Worse, if you become the docile girlfriend he realizes he can trust completely, he’s as likely to return to his own comfy pattern of having many relationships as back-up (still with the tired excuse of HE doesn’t want to get hurt. Who does?).
The guy’s immature and not ready for a long-term relationship, and – since you already have doubts – there’s no point in dragging it out.

My two best friends started dating at 12, for five years. It was a good relationship; I’ve never seen either of them happier or more in love. They broke up with no apparent reason, remained close friends, and were inseparable.
Three years later, she still hasn’t dated anyone, and neither has he. They’re often mistaken as a couple.
Six months ago, they both decided to not see or talk to each other again, in order to really break it off. However, none of their families, or friends like this.
He’s become more of a workaholic without her. He doesn’t see family, other friends, and I only see him every two months.
She hasn’t smiled at all, and barely talks. Everyone is worried.
When I’m with each of them, they ask about each other. Yet both stubbornly believe that they don’t need to see each other.
How can I help them? 

- Concerned

A good friend asks the right questions, but doesn’t supply the answers. These two have an intense link they need to work out. However, given their youth and inexperience with other relationships, they may need professional help to guide their thinking.
It seems they made family of each other, so their break-up feels like a huge loss. That doesn’t mean that they’re meant to be together forever, and they seem to be mature enough to have some inkling of this.
Yet, both are grieving, and can’t discuss it with the person they’re used to turning to for comfort. That’s why separate individual counselling would be an important help to both of them.
Ask each how they’re doing, who they talk to about it, what strategies they feel they have to handle it, whether they’d like to be helped by an experienced therapist who’d understand their pain and would know the process to move them forward. Then, back off.
It may take time for either one, or the other, or both, to react. But you’ll have planted helpful seeds. No matter what they choose to do with them.

My stepdaughter, 15, HATES me. After five years, she’s rejected her father and I and wants NO CONTACT with me. The story is long and complicated. 

- Distraught

It’s a common story about divorce, hurt, mistrust… all on HER side, during already-turbulent teenage hood.
On YOUR side are too-high expectations, disappointment, hurt. It’s not a situation that can be “fixed” quickly or easily, in anyone’s story.
Her father needs to send letters even if she doesn’t respond - she’ll likely open some, whereas phone calls can be ignored and emails deleted. He should write, briefly, that he loves and misses her, then share small details… e.g. “We saw a movie I think you’d like,” or “one day I’d like to take you to this restaurant downtown…” etc.
After they eventually re-connect, she must acknowledge your presence with politeness. Try to be an understanding, caring adult in her life, not a stepmother.