Ask Candid Candace: How to energize a couch-surfer and a decades-long high school crush

Dear Candid Candace: Need your advice on a career question. Not for me, but for a friend whose son quit a good paying corporate job, at the tender age of 29, in a kind of early mid-life crisis— “ I want to find a job with more meaning” type revelation.

My friend seemed to be ok with this, his wife not so much, but the question is this: It has been over 6 months now and still no work and no real concentrated job hunt.  Do the parents continue to stay hands off and supportive (as they have done so far), or is it time for a more strict sit down conversation with their soon to be 30 year old?

Signed: Asking for a Friend

Dear Asking for a Friend: First off, kudos to your friend and his spouse for not immediately turning into the Parental SWAT Team when their son hit the eject button on Corporate Flight 101. Taking time to figure things out is not only brave—it’s also commendably human. But now, six months in, the dreamy fog of existential exploration might be drifting a bit too close to the “Is this still just a phase?” alarm bell.

Here’s the deal: Support is good. Unconditional love? Excellent. But enabling prolonged couch-surfing and vague “soul-searching” without any signs of, you know, movement, can eventually do more harm than good. Even purpose needs a plan.

So, what’s a loving parent to do? It might be time for a gentle-yet-firm sit-down. Not an intervention (no need to cue the dramatic music), but a heartfelt conversation that says, “We believe in you, and we’re here for you, but let’s talk about your next steps.” Ask questions like: What have you learned in this time off? What direction are you leaning toward? How can we support you—without doing it for you?

Think of it less as “tough love” and more as “compassionate nudging with snacks.”

After all, your friend’s son is about to enter the Big 3-0—the decade where dreams should include Google Calendar reminders and a health insurance plan.

Wishing your “friend” and their free-spirited offspring the best of luck. May meaning be found, resumes be updated and rent eventually paid.

Dear Candid Candace: I’m going to my 40^th high school class reunion soon and just saw on the invite acceptance list that the girl I always had a crush on in high school is going to be attending!

I went to a large high school, and I was pretty shy around girls back then, so I never even had a conversation with her through all 4 years. I was thinking of, at some point during the evening, just going up to her and introducing myself and telling her about my crush on her from 40 years ago.

Is that appropriate? And if so, what is the best way to approach her and start the conversation?

I should mention I am happily married now, as is she, and there is no ulterior motives here.

Signed: Reliving the Crush

Dear Reliving the Crush: First of all—how adorably brave of you! I love this for you. A high school reunion is practically the Olympics of nostalgia, so if there was ever a time to dust off a decades-old crush and bring it out into the open, it’s now. Plus, you’re not trying to sweep her off her feet—just to share a sweet, harmless little truth that’s been sitting quietly in your memory since bell-bottoms were still a thing.

Now, about your game plan: subtlety and sincerity are your best friends here. No need to burst in like a long-lost Romeo with, “I loved you in homeroom and I just needed to say it before one of us keels over!”

Instead, try this: Find a casual moment—maybe she’s by the punch bowl or checking out the old yearbook display. Approach with a smile, introduce yourself ("Hi, I’m Jon—we went to school together, though I was way too shy to ever say hi back then..."), and then lightly drop the nostalgic nugget. Something like:

“I just wanted to tell you, in the spirit of all this reminiscing, I had the biggest crush on you back in high school. Never got up the nerve to say a word to you—but hey, 40 years later, better late than never, right?”

Keep it light, keep it short and smile like you’ve just set down a small secret you’ve carried in your pocket for four decades. Most likely, she’ll be flattered, maybe a little bashful, and you’ll both walk away feeling good—and maybe even share a laugh about the past.

A little innocent reminiscing never hurt anyone—especially when it's served with a wink and wrapped in sincerity.

Now go enjoy your reunion, you charming time traveler.

Ask Candid Candace is presented by Randolph Street Market- See their full schedule below!