I’ve been seeing a nice personable woman for a year and thinking of a future with her. She’s in major debt, possibility facing job loss under current economic conditions. Should I keep dating her, knowing her financial well-being is also important to me? 

I sympathize yet cannot see myself supporting her unconditionally should we hook up more permanently. I help her out with odd jobs around her house. Do I have an obligation to help her financially?

We’re mid-40s, I cannot afford another person’s debt.

- Indecisive

You use the F-word over the L-word about her – you’re not ready to commit, and should not mis-lead her. 

When you L-ove someone enough to spend your future together, you work on any obstacles together: e.g. you’d advise her to get credit counselling to lower her debt. You’d discuss back-up plans for her to find other work if she loses her job. And you’d even figure out if you could live on less for the sake of sharing your life (and money) with her.

But when F-inance is your main passion, it’s best to cut your own losses and move on. If that suggestion doesn’t sit well, check your feelings instead of your bank account. It’s better to face an uncertain future with someone you love.

I’m 20, married for one year. 

From age 16, this one guy said he loved me, asked me many times to be his girlfriend but I always turned him down. When I met my then-boyfriend (not my husband), this amazing guy met his girlfriend. We both dated our partners for a year, his girlfriend got pregnant. That’s when I realized I truly felt something special for him.

We ended up hooking up, both of us still in other relationships.

When his daughter was due, he informed me he’d move in with the mother... I was devastated. But I stuck by him because I love him.

Previously, he’d asked me to move to Arkansas with him and start a new life together but I was scared.

A year after he moved in with his girlfriend, I suggested we go to Arkansas, but he couldn’t leave his daughter. That’s when I decided to marry my husband.

I still love the other man and can’t see myself without him, but now I’m pregnant by my husband and my love told me things will never be the same anymore.

I don’t want to lose him. I’m willing to leave my husband at any time, but he can’t do the same for me.

What do I do now that I’m pregnant?

- Puzzled Mom-To-Be

Get out of Fantasy Land and into the real world of raising your baby. Hopefully, Nature’s demands on you to grow up will help you see what a loving, lasting commitment is all about. 

It’s NOT about getting obsessed with someone when you realize he’s taken.

It’s NOT about running away and thinking you’ll escape all thoughts and responsibilities for those you left behind.

Your “love” has been a teenager’s passion – “deciding” to marry someone because you couldn’t convince another to give up his child, was proof of your immaturity.

Give your baby a chance at a healthy, happy home with two loving parents (wasn’t that the ideal you always thought you wanted?). If your marriage can outlast your daydreaming escapism, you’ll all be lucky! If not, focus on becoming a responsible Mom and mature, independent woman, not the child who’s been trying to “win” back a high-school crush.

When a person writes you about their own relationship problem, you offer straightforward, action-oriented advice. 

However, when someone writes about the situation of a friend or relative, you generally recommend they stop being judgmental, just offer support instead and let matters play out. But it’s so hard to stand-by silently and watch someone get hurt, particularly if you’re older with more life experience.

- Loyal reader in Chicago

It’s hard to generalize about my own approach, as I do give each writer’s question individual and serious thought. However, I’ve found through my own experience and that of countless others plus professional counsellors, that unless people specifically ask for advice, commentary, and/or intervention, speaking up is usually not helpful. It creates defensiveness, or worse, rebellion.  

Support allows a person to come to his or her own conclusion, while unsolicited advice can destroy your relationship, so there’s no future chance for being asked to help.