She’s been my friend for 14 years; we grew up together, dated a while, but remained friends. 

When she got a boyfriend, I became her protective brother; when he dumped her, she sought me for comfort. They got back together, lost their virginity to each other and he soon broke up with her again.

She dated for a year but never found “the same happiness.”

Recently, she and her ex got back together again because, when he learned she had a new boyfriend, he “realized” that he loved her. They’ve had sex again and now I feel history will repeat itself.

I know my friend is emotionally attached to this man because he was her first, but I don’t know how to tell her that she needs to move on instead of being stuck with someone who keeps messing with her feelings.

- Stuck in the Middle

Take heed of the expression, Too Much Information: That’s what your friend is telling you, and what you need to back away from hearing. It’s not the job of a friend to run interference with her relationships. You can support her decisions, or back away. 

Yes, she’s emotionally attached and needs to come to terms with whether that’s hindering her judgment; but you’re also too emotionally involved in her life.

Go your own way more, talk about other matters with her. Your being there as a constant shoulder to prop her up, listen to her stories, etc. may be contributing to her inability to stand back and see this situation as clearly as you think she should.

OR, she’s in love with the guy and that’s her right to pursue.

Six months ago I started my own business due to our children’s serious health concerns; I needed to be flexible and close to home. Previously, I was working full-time. 

I love what I’m doing now, but financially, I’m not contributing monthly what’s expected of me. My business plan projects sales to meet my financial requirements at the two-year mark.

My husband and I just recently agreed, that although my income wasn’t yet what he’d expected, being here for the children was most important, given the hospital visits, doctor’s appointments, etc.

Yet I feel he resents my flexibility, time-off and the passion I have for my job. Today, he said I need to give up my business and get a full-time job. Although I’m aware of our monthly payments, he’s the one that pays the bills.

I’m angry, sad and confused. I already have another part-time job and am willing to add another. I feel I’ll resent him if I give up my new business under these circumstances.

- Struggling

Take the discussion outside… to a professional financial planner. Your husband may be truly pressured under the current financial constraints, but there may be other ways to resolve this. 

Your children’s needs are primary here, and you both need to be firm on that. A full-time job for you could create difficult time conflicts and huge stress for everyone involved.

Yet, the kids are not an excuse for you to hang onto something if it truly isn’t working.

A financial planner will help you look at many options... everything from sticking with new venture by taking a business loan, to putting it on hold awhile and working only the part-time jobs, until the children are more settled health-wise.

Most important, focus on essential needs here, not on who “wins” this argument.

I’m a guy who recently broke up with my boyfriend, and have since moved on. I’m interested in someone new who has everything I want. I’m 15, he’s 18. 

As mature as I am for my age, I still think it can’t work. He’s all I think about, and it would be amazing to be his boyfriend.

Should I ask him out or accept that it’s not going to happen?

- Confused

Good relationships rarely develop when one person is full of self-doubt. You say you’re mature, yet you’ve fixated on someone whom you consider unattainable… likely because of differences in your ages, school level, social networks etc. I suspect that when you say he has “everything I want,” you mean, everything you want to be, yourself. 

Consider this a crush on someone to admire but not to approach, as you’ve already set up expectations of failure and will only get hurt.