After three years of dating my boyfriend, I feel increasingly resentful, used and HURT, because he still hasn’t proposed.  

He’s in his early 50’s, never married; dating a single mom and being involved with my child, 7, has been a huge milestone for him. I said from day one that I want to get married.

After two years, we moved in together but I started to feel very uncomfortable without being engaged.

He refers to me as his wife when I’m not around.

Money’s not an issue - he’s very generous with us.

When my patience went, we had more and more fights and I got more and more bitchy. So, the more he DIDN’T want to marry me and the more pained I felt.

Lately, we’re finally getting back on track but I’ve lost that little girl's dream of a beautiful wedding with him.

He’s the best thing that ever happened to me, a great guy with a heart of gold, who loves my daughter as his own. I think he will propose one day.

But now I don’t know how to deal with my resentment. I want to punish him by saying NO when and if he finally proposes, but at the same time I’m hoping he will.

- Unwanted

Get a grip on the good stuff – he loves you, has stayed through this turbulent period, and things are improving. 

Your “punishing him” notion is foolish and self-defeating, so drop it.

Instead, show this guy the assurance he seems to need, that marriage is far more than the fantasy wedding you imagined… it’s the path to make you and your child feel secure, to commit YOU to him as well as HIM to you, such that the traditional part about “sickness and health, good times and bad,” really holds true for all.

My boyfriend of two years is a separated single father with shared custody. 

I feel that he loves me, but he’s working through a lot of pain from his marriage and is frightened of commitment. He’s also very protective of his daughter and, of course, wants to spend as much time as he can with her.

But I love him and though I’m not looking for a ring, there are long stretches of time when I don’t see him and feel like I’m an afterthought.

I alternate between thinking I should end it because we aren't on the same page, and wanting to enjoy what I have.

- Confused

Separation and custody issues take a toll that requires time for healing and for settling the children involved. Your boyfriend’s priorities are normal under these circumstances; eventually, he’ll get more comfortable with the situation and be more at ease about his right to have a relationship that includes his child, as well as takes some adult time away from her. 

But it may be too soon to push him on this. What you need – if it’s enough for you to hold onto for now – is a clear understanding between you. Reassure him that you aren’t after a ring, just the security of knowing his feelings are real, and that he’s not just fulfilling his recreation (and sex) needs with you.

He may be too wounded and wary to give you that assurance. If so, my advice is to walk away, lest you later discover you were only the Transition Woman.

If it’s more than that, he’ll come after you.

I’m male, 40, and have never been married. 

I’ve had a few dates with women - we have common interest on these dates and seem to hit it off. But when I later contact these women for a second date, their response is no.

Am I doing something wrong?

- Frustrated

Your expectations may be out of sync with reality. Most people can get along on a first date; it’s a matter of being polite and showing some interest in the conversation. But that doesn’t imply chemistry. 

Try “practice dating” by going out with a female friend, neighbour or cousin, and focus on simply having a good time.

When you’ve learned to relax more, socially, try dating again.

Treat the first meeting the same as a friends’ get-together, no pressure, and then suggest a second date to follow up on something in which you both expressed interest… even if it’s just a walk.