I’m a shy 31-year-old male who’s had only one relationship, starting with two years’ just dating, then four years in university where we lived together off-campus.

After graduation we moved to different cities, having recognized that we’d become “best friends” only.

I’m hoping now to meet someone special. I go to a nearby dog-walking park with my Beagle every morning hoping that we’ll meet “The One.”

But I lack any skills at chatting up females to whom I’m attracted. Your suggestions?

Shy Guy

Enlist your dog. Beagles are generally very friendly, active dogs. Some women choose them because they’re considered “sweet.”

If someone else has a Beagle, chat enthusiastically about them. You’ll meet neighbours, possibly some new females. Suggest getting coffee nearby. Even in a group, casual conversation can open doors. Just don’t come on too strong.

Due to a messy marriage break-up, my brother’s been estranged from his only daughter since she was eight-years-old.

I’ve kept in touch with my niece who lives across the country from me, through birthday/Christmas emails and gifts.

I’ve always given her lots of “space” in our relationship with no obligation but an open door. She always responds graciously and lovingly, for which I’m grateful.

She very recently became engaged and I’d love to send her a monetary gift to help with the wedding. But I’m afraid she’ll feel obliged to invite me, which I only want if she’d like me to attend.

Also, should I tell my brother that she’s engaged?  He’s not in contact with her nor on social media.  How should I handle this?

Delicate Family Situation

You’ve already proven your caring and commitment to your niece through staying connected, gifting her on special occasions, and, most respectfully, offering her “an open door” with no strings.

Your engagement gift including financial help with the wedding is generously in keeping with your relationship. Barring any potential interference due to the long-ago “messy divorce” of her parents, I’m sure that she’ll be delighted to invite you. Hopefully, her mother will agree.

However, your brother’s long estrangement from his now-adult child may make it impossible for him to connect with his daughter about the wedding.

Nevertheless, alert him to the engagement news. He may not consider re-connecting but, just maybe, he’ll send her congratulations and a gift.

You’re the only link to his daughter, because of your open-hearted efforts.

Say that this is the opportune time for him to reach out to her. So, encourage his coming forward as the father she did nothing to lose.

After our 40-year relationship, my then-partner sought someone half his age, unemployed with young kids. We have four adult children and 12 grandchildren. I work full-time, he’s on disability.

Ever since I accepted my current position eight years ago, he’s used it against me. But he continued to go out with friends throughout our relationship. I trusted him.

I’ve always worked because he couldn’t/wouldn’t move out, since I then earned too much money for him to get disability.

I tried to make it work. Then he cheated.

Cheating User

Seek a professional social work therapist/ psychologist/psychotherapist to discuss your current choices.

Your ex-partner is using your earnings to support himself and enjoy socializing with his friends. Any chance of “making it work” is long past.

Seek a lawyer about any legal obligations to financially support him. Talk to your financial advisor. Then dissociate from him to the degree that the law allows.

My now-close friend and her ex-husband divorced 15 years ago. He left this city soon after, but recently moved back.

The first time he and I met at a house party, we clicked! I’m very interested in him but worried that I’ll lose my friend if he and I get together. Should I just resist the chance of hurting all three of us?

Uncomfortable Choice

There’s a real risk that your friend will feel you’re breaking a loyalty code. She may prefer privacy about his chance to tell a different story of their divorce, from hers.

Much depends on whether she’s happily partnered with someone else. If yes, mention the chance meeting and mutual interest. Watch her reaction closely as it may already be too late to not hurt the friendship.

My own take is this: It’s way too early for both you and this man to assess his or your interest.