We've been dating for nine months. When I’m with him I feel respected, beautiful, and interesting.

A close friend, who was then dating him, introduced him to me three years ago. They were drifting apart and she thought I'd be a great match for him (she was right, but it's still odd).

I became his friend, but didn't want to get involved with someone who'd just left a long-term relationship with my dear friend.

He and I finally got together two years later, and she was overjoyed.

We’re still good friends, and they’re still good friends. We often catch up together and have a wonderful time. I care about and trust both of them.

I’m falling for him.

I know they’d never deliberately hurt me but sometimes I feel a little jealous of their past.

They understand each other so deeply it can sometimes be difficult to watch them interact.

I've yet to raise this with him. It feels unreasonable of me to feel jealous.

Also, I don't want them to feel compelled to change their behaviour.

They’re not doing anything wrong, their friendship makes them happy, and mostly, it makes me happy, too.

I’m unsure how to proceed.

Uncomfortable

Here’s the thing about honesty – it’s clearer than vague discomfort, and it shows respect for everyone involved.

If you want a future with him, speak up now.

Say you trust him, and also trust her.

But confess that your feelings for him have reached the emotional level that allows some uncomfortable jealousy to emerge.

You want them to be friends, but you also want to know that your romantic relationship is a priority for both of you.

You want your time alone with him to be special and different from the “catch-up” get-togethers.

If a gentle and honest conversation about this makes him uncomfortable, you better find out why, now.

I’m a female, 64, with a younger brother, 58. We haven’t been on great terms due to his standoffishness.

He’s going through his second divorce, has multiple health problems, and recently sold his business. He smokes, doesn’t exercise, doesn’t eat healthy food.
Not an easy life.

I tried to keep in touch to express concern, and asked him to have a meal with me as my guest or meet to talk.

He mostly doesn't respond. I got a late RSVP to my wedding party (my second marriage and I’m very happy).

He had a mild heart attack six weeks ago.  I contacted him, asking if I could do anything to help, but heard nothing back.
Recently, he asked me to drop in.

When I did, he proceeded to "divorce" me, claiming I’m the cause of all the stress in his life!!

I’m gob-smacked and very hurt.

I said the door to communicating was still open if he wanted, then left. I’ve heard nothing from him since.

Is the situation a lost cause?

Sib-less 

The “situation” is about him, not you. What persists are his health problems and personal stress.

If your health-oriented happy life, plus offers to help make him feel judged, even jealous, that’s his choice.

It’s likely been a part of his history which you didn’t realize, e.g. him feeling second-rate or unfavourably compared to you in the past.

Just check in on him occasionally, either through his friends or other family, or a brief email.

Perhaps offering “help” or advice isn’t what he can accept from you when he’s so low… maybe just showing your interest is all he can handle for now.

FEEDBACK Regarding the discouraged "Newbie” (June 24):

Reader – “I went through what you’re experiencing. It’s no small thing.

“I eventually took a civil-servant job part-time. Five years later, it’s a full-time career with a pension, benefits, and security.

“I'm late-30s, married with two young daughters. It's amazing how freely people will judge you, and can make you second-guess yourself. Don't!

“My husband and I were both late-bloomers, and met when we both felt like you – asking, how are we going to make it?

“We chose long-term happiness over stressful ambition.

“We work blue-collar jobs, rent our home instead of own. Our “luxuries” are good music, a few drinks, and honest conversation.

“Don't be too hard on yourself. If you’re doing your best, and working towards some goal, that's enough.

“Don't measure yourself against others – it's a dead end. The greatest success you can have is being true to yourself, and being happy.”