I’m dating a man who doesn’t get my literary references.

He’s a very nice guy – good-looking, separated from his ex, ready for a relationship, as am I. We’re mid-30s.

We have good sexual chemistry, but both agree that we need to go slow.

So we talk a lot, watch some movies, go for walks, he’s even been cooking for me on some dates.

The only awkward moments have come when he didn’t know what I was talking about and got embarrassed.

Once I was talking about books I’ve read that were Booker Prize winners, and why I found them so superior to popular thrillers that get turned into film franchises.

That’s when our educational differences surfaced. He’s street smart, good at his business (he’s a building contractor), and an avid sports fan.

I’m a professional and an avid reader, though I enjoy watching some sports, such as tennis finals.

Do we have a chance together?

Too Big a Gap?

It’s only a problem if you make it so. Enjoy the differences.

Don’t have attitude about his level of understanding. Share your thoughts freely, and let him absorb whatever he chooses.

It’s a way for both of you to grow.

Learn enough about his sports to at least ask how a game is going.

Appreciate his knowledge and passion, and he’ll appreciate yours.

My partner of almost four years is 37; I’m 27. I have a number of red flags, but fear the intense loneliness that’d follow my ending things.

He loves me very much. He’s good to my family and me. I’m certain he’s in this for the long-term.

But I don't think we push each other to be our best selves. Is this a realistic hope?

Also, he’s years behind on his taxes and carries past student debt.

He’s now completing a second undergraduate degree (part-time), with a likelihood of post-graduate studies.

He’s also working to pay for the classes. He moved in with me this past August.

I’d believed we’d be splitting the cost of rent and utilities.

He hasn't yet contributed to anything aside from some shared food costs.

He says he can start contributing in the summer, but fall’s university expenses will quickly follow.

I want to support him because I love him, and my costs are similar if I were living alone.

Yet it bothers me that he never asked if this arrangement would be okay.

Had he been contributing, I could’ve fully paid off my own student debt this month.

I'm also feeling some resentment when the apartment gets too messy, or he's too busy studying to spend quality time together.

I know now that I’ll never be able to move our relationship forward until he sorts out his finances.

Ending things for that reason feels too shallow. However, am I damning myself by not speaking up?

Feeling Stuck

It was up to you to say from the start that you didn’t wish to totally support him, so “some” monthly contribution was necessary.

If he didn’t have you, he’d have worked this out.

Speak up now, or your resentment will divide you anyway.

Say he must devise a financial plan that allows some cost sharing.

Offer suggestions – e.g. more work hours, or a second job, e.g. tutoring online.

Be realistic. This won’t allow for more “quality time” together, though a more equal relationship will enhance your feelings.

Either you love him enough to ignore the small stuff (messy room sometimes) or your exaggerated fear of loneliness is going to end up very costly.

I'm married with two kids and pregnant. My husband works full-time; I’m soon graduating from my Master's program. I'll look for work after the baby’s born.

My mother’s offered a generous graduation gift of down-payment on a house.

But my husband's wages were averaged over two years when he was earning less, and we qualified for little mortgage money.

Mom’s suggested putting the house in her name while we pay the mortgage and buy the house from her later.

But now we’re faced with what to tell people.

We consider it our home, but don't want to lie. I'm uncertain what to tell my best friend or grandparents.

Embarrassed

With your closest people, just say, “Mom’s helping us.”

It’s nobody else’s business.

Those who are mortgaged to the roof don’t tell anyone. Yours is a practical arrangement of trust, from a mother, to you two and her grandchildren.

It’s loving and private.