I’ve been dating a wonderful man for three years.  We get along very well, he’s caring, kind, and above all, very honest.

I care for him deeply and enjoy spending time with him, but I’m starting to feel like we’re in different places in our lives.

I’m a single mom, relatively established in my career and earn a decent salary, which allows me to pay all of my bills, take care of my family and still save money.

He’d spent a few years working overseas, and returned a few months before we met.

He’s a hard worker employed by a big company, but often says he’s having difficulty making ends meet.

After paying all of his bills he says he has little left over for “fun.”

I’ve never put much emotional value into money.  As long as I have enough to take care of myself and my family, I’m happy.

I was previously married to a man for whom money and possessions were of high importance. I let myself fall into those materialistic trappings at the time.

But once that relationship ended I realized that was not who I was.

There are many things I want to do together in my current relationship - go out to shows, music events, trips - that we often cannot do because my boyfriend doesn’t want to go.

I have no problem paying for the events if I can. For me, the time spent together is more important than the dollars spent on the event.

But I know that it’s an issue for him.

It hurts me to think that I’ll have to share those experiences with someone else because of money.

He does so much for me: he makes me dinners, helps fix things in my home, etc. I want to be able to say that I consider this my way of paying you back.

But I also don’t want to wound his pride, if that’s the issue.

How do I navigate this financial difference that’s affecting us, without making him feel like I’m steam-rolling him and his feelings?

Money and the Relationship

No relationship benefits from steam-rolling someone to change.

His pride is as important as your entertainment wishes.

Every new couple has to balance some different “values.”

Your ex’es attachment to the trappings of an expensive lifestyle changed your values. Meanwhile, your current boyfriend hasn’t had the kind of money to even think about these matters, as you do.

Yes, he helps you out but does so from the heart, not from a desire to be “paid.” Even a veiled suggestion of his expecting any payback, might insult him.

So, tread lightly. Instead of offering to pay for all the entertainment events and travel you’d like to enjoy as a couple, choose one special thing for Christmas or his birthday, as your gift.

And don’t go for something so costly that he’ll feel emasculated by your over-generosity.

(With some of the outings you’d like to enjoy, organize girlfriends or family members to join you).

Also, when you two do have simpler dates just enjoying each other’s company, try to discover if, maybe, he honestly does not share your same interests.

If so, his response isn’t only about having far less disposable cash than you.

And you two still need to find more common ground for maintaining a long-term relationship, instead of your focusing on the current financial difference.

Give him a chance to say how he sees your future together.

Readers’ Commentary, Part 2 Regarding the desires of emerging teens for more freedoms (November 7):

“Our son, early-20s, is a successful pilot. We said “No” when he wanted to take easier academics in high school because his friends did.

“It caused friction in the house. We weren’t his best friends, but rather, we were caring parents there to support him but also let him know when he crossed the line.

“He’s now a mature, funny, considerate young man who has independently set himself goals and is well on the path to meeting them.

“He sees his friends regularly and is well-regarded by his flight captains and employer.

“He won awards at college because he loved what he was doing and applied himself to it. He dug down deep and persevered when he needed to.

“He learned those skills both at home and through team sports.”

Ellie - Firm standards, but obviously set through loving and logical explanations.