Dear Annie: I’m a 47 year old woman and have been with my boyfriend, “Greg”, for almost six years. I’m really happy with him and I’m at the point where I really can’t imagine being with anyone else. There’s just one thing: he hasn’t proposed, and I don’t know if he ever will.

It’s gotten to the point where I almost feel desperate for him to propose, but I don’t want to ruin what we have by pushing him away. I also don’t want to waste additional years in a relationship that has no future.

I talked to him about it once, and he kind of brushed it off and said, “One day, when the time is right.” » But I’m starting to feel like maybe a “day” will never come? He’s already married once and had a messy divorce, and I’ve noticed that he still seems a little bitter about the whole concept. Every time someone we know gets engaged, they make a comment like, “Let’s see how long that hard. »

Recently, several friends and family members have asked us when we are going to get married, and it’s so embarrassing for me that I don’t have an answer. A friend advised me to give him an ultimatum, but I’m too afraid it will backfire on me. I love him and I don’t want to lose him, and I know he loves me too.

How can I approach marriage in a way that doesn’t feel like I’m pressuring him but lets him know how important this is to me? Am I wrong for wanting this commitment, or should I just be happy to have this good relationship? — Wait and wonder

Dear waiting and questioning: For some people, marriage is the ultimate symbol of love and commitment. Others might take it or leave it. Still others are fundamentally opposed to it, arguing that they do not need documents to prove their love.

The only way to understand Greg’s position is to speak to him directly. It sounds like he’s holding on to some bitterness and fear from his first marriage, which can be overcome through communication and the help of a good therapist.

If marriage is non-negotiable for you, tell Greg that as soon as possible. You don’t want to stay with someone who ultimately can’t give you what you want.

Dear Annie: I have a recommendation for your older readers who are considering marriage: I strongly suggest they talk to a financial advisor about the monetary perils of marriage.

Married people are equally responsible for each other’s debts (think medical bills). There’s nothing like suddenly becoming a widow and facing crushing medical bills. Long-term care also leverages the assets of both people if they are married. I know two couples who divorced because of this.

Losing even a few hundred dollars a month could make a big difference in their standard of living. By all means, have a commitment ceremony, but seniors need to be aware of the financial risks of getting married legally. This could threaten their well-being. — Practical

Dear Practice: Thank you for offering your perspective. All couples, regardless of age, should have a conversation about finances before deciding to get married. The more money is at stake, the more professional advice is necessary.

“How can I forgive my cheating partner? » is out now! Annie Lane’s second anthology – featuring her favorite columns on marriage, infidelity, communication and reconciliation – is available in paperback and e-book form. Visit for more information. Send your questions to Annie Lane at [email protected].