Advice columnist Allison Task

For Montclair Local

Allison Task is a career and life coach in Montclair who hosts the WMTR radio show “Find My Thrive.” Her website is Need advice? Send questions of no more than 150 words to, or to us at

Dear Allison,

For somebody like me, middle-aged but ready to begin his second act, how should I proceed? With work, writing and raising elementary-school-aged twins, I don’t have a ton of time for dating women.

Man Ready to Restart

Dear Ready,

Since you’re a writer, I’m going to read a lot into the way you built those two sentences. You’re asking about your second act, and proceed to list the components of your life. First you list all you’re “doing” and my assumption is that you’re satisfied with how you’re currently working, writing and raising twins. You ask about dating in a roundabout way, stating that you don’t have a lot of time for it, and yet it makes your top four list of second-act activities.

Dating, it seems, is the thrust of your query.

So, how does a divorcing (or separated or widowed) man with a lot of middle-age responsibility date? First a moment of truth:

Statistically, know that you are sought after. There are more women looking for you than men competing with you for dates. And yes, that includes the data points of “married once before” and “having children.” That statistic only improves as you age, especially “if you drive and have hair,” as the ladies in Boca have informed me.

A female client of mine, who would be very open to dating someone like you, recently signed up for a local speed-dating event. Two weeks prior to the event, she is still on the wait list. Why? There are more women like her than men looking for her.

Recognizing the opportunity inherent in your situation, I ask you to consider: what’s your goal for dating women? Gaining dating experience? Sex? Female friendship? Or are you ready for longer-term companionship and commitment? If you don’t have much time for dating, then be strategic about why you’re dating. It’s the best way to pursue the type of situation you seek.

And while you’re taking stock, what do you have to offer said person? Once you know what you want and what you have to offer, there are many ways to connect the dots.Finding the person may actually be easier than identifying what you’re looking for.

And remember, there’s always speed dating. Fun, efficient and, from what I’ve been told, there are plenty of seats at the table for you.

Dear Allison,

How do I address someone else’s divorce? My daughter was in pre-K with a child whose parents are going through a divorce. I bump into both parents, and though I haven’t been told directly, I’ve heard. How should one (if ever) address change of marital status? Especially when not a close friend?

Concerned and Considerate


To best answer your question, I spoke with some divorced parents and was surprised to learn that people use divorce as an opportunity to ask intrusive questions about the marriage. Imagine if someone asked a pregnant woman for details about her sex life. “Well, it’s obvious you’ve had sex, so…what positions do you like?” “Getting a divorce, eh…was she a total psycho or what?”

Not that you’d take that approach, but I share this so that you can empathize with what those who’ve recently split can be braced for.  People may also receive a lot of well-intentioned, “Oh no!”, “Ouch!” or “You know, I never thought he was good enough for you.” They are sometimes put in a position of managing others’ disappointment or hearing “told you so.”

Are you cringing? I was also surprised and pained to hear this. Divorce is hard enough; these responses don’t make it any easier.

And so let me ask you, what is your goal in addressing it? To help? To recognize that single parenting is difficult, and the kids (and parents) might be experiencing some stress? If so, then jump on in there, earnestly offer help and see it through. Help is rarely refused, especially when it’s of the child-care variety.

Otherwise, it may be best to wait until you’re told, and find a calm, supportive way to respond to the information. An earnest, empathetic “I’m sorry” can go a long way.

The divorced parents I’ve asked shared that their preferred way for casual acquaintances to address change in marital status is by not addressing it at all, thus relieving the divorcing person from having to talk about it or explain it.

(I think you knew this given your parenthetical.)