• Skip to main content
  • Skip to secondary menu
  • Skip to primary sidebar
Chicago Sports Today

Chicago Sports Today

Chicago Sports News continuously updated

  • Bears
  • Baseball
    • Cubs
    • White Sox
  • Basketball
    • Bulls
    • Sky
  • Blackhawks
  • Colleges
    • DePaul
    • Illinois
    • Loyola
    • Northwestern
    • Notre Dame
    • UIC
    • Valparaiso
  • Soccer
    • Fire
    • Red Stars
  • Team Stores

Asking Eric: Will he ever propose?

September 18, 2025 by Chicago Tribune

Related Articles


  • Ask Anna: Should I stay married to someone who doesn’t desire me?


  • Asking Eric: Longtime friend always has to have upper hand in conversation


  • Asking Eric: New husband wants to travel without me


  • Asking Eric: How can I nip these interactions in the bud?


  • Asking Eric: Mother-in-law wants to bring boyfriend to Thanksgiving

Dear Eric: My good friend has been with her boyfriend for more than 20 years. She finally moved into his house after her mom died a year and a half ago. They attend each other’s family events – weddings, funerals, birthdays, sports events, work parties – and he tells her he loves her.

He’s had every detail of his future wedding already planned out, including who the groomsmen will be and where he wants to get married. Unfortunately, after every holiday or special event, there’s never an engagement ring for my friend. His girlfriend before my friend was a thinner blonde who dumped him.

After more than 20 years, do you think he’ll ever propose and get married to my friend?

– Bridesmaid-in-Waiting

Dear Bridesmaid: Sure, it’s possible. It’ll be even more likely to happen if your friend and her boyfriend have an honest, frank conversation about their wants and the details of their individual timetables.

While it might seem obvious that, after 20 years, he should want to propose, especially considering he’s already designed a dream wedding, the only way to find out what he’s really thinking is talking to him about it. This is also the only way for your friend to let him know what she’s thinking.

Often in long-term relationships, we start to assume our partners have enough data to be mind readers. And sometimes, too, we assume we know every neuron firing in the head resting on the opposite pillow. But, of course, that’s not fully true.

Even if someone wants to have a surprise proposal, and all the fanfare that that entails, it’s crucial for the health of the relationship to keep lines of communication open.

Dear Eric: I’ve heard, informally, that my nieces and nephews have collectively decided that the entire family (including me) will gather for the college graduation of one of my great-nephews in May. I wasn’t involved in that decision, but that’s OK. It’s not my child or event. (I don’t have children.) I am also the only living uncle.

I have no interest in going. These family events involve so many people; it is difficult to spend any meaningful time with anyone. In addition, it’s on the other side of the country, and the graduate-to-be and I have never been close. He has barely spoken to me at other gatherings and has never acknowledged the (cash) gifts I have sent over the years for birthdays, Christmas or his high school graduation. Although that seems to be the rule anymore, and not the exception.

This will be the first of such graduations that will happen almost yearly for some time. Not to mention the eventual weddings.

The dilemma is, if I skip one or two but go to others, there will likely be hard feelings among relatives. And if I go to this one (reluctantly), am I obligated to go to all of them?

Fortunately, it’s not a financial burden. And I’m retired, so time is not an issue. But it feels more like a root canal appointment than a good time.

I feel like there is no “everyone happy” scenario here. Am I missing a solution?

– Go or No

Dear Go or No: If you don’t want to go, don’t go and tell them the dates just don’t work out for you. You don’t have to make up a fictional vacation or some other elaborate excuse. But you have your own life, schedule and priorities and it’s true that this event does not fit into those.

By addressing this head-on and early, you also have the opportunity to send your well wishes, and a gift if you so desire. You also have the opportunity to set a precedent that’s fair and that works for you. That precedent: you’ll come when you can. There’s nothing stopping you from making the upcoming milestones feel special for your great-nieces and great-nephews in a way that’s specific to you, your relationship and your capacity.

To your point that there may be hard feelings: everyone’s feelings are their responsibility. If you’re upfront with your relatives and make a good faith effort to honor the celebrants, you don’t have anything to feel bad about.

Dear Eric: In response to “Grieving Granddad’s” letter regarding the loss of his longtime dog companion, thank you so much for recommending adopting an older dog. I would also add that he, or anyone who isn’t sure about a fur-ever commitment but wants dog(s) in their lives, might consider dog foster care.

– Foster Dog Parent

Dear Foster: A great suggestion. Another note that came up in the responses to this question is that everyone, of any age, should make sure that there are plans in place for a friend or relative to take care of the dog if the owner is incapacitated or dies.

(Send questions to R. Eric Thomas at eric@askingeric.com or P.O. Box 22474, Philadelphia, PA 19110. Follow him on Instagram and sign up for his weekly newsletter at rericthomas.com.)

Filed Under: Bears

Primary Sidebar

Recent Posts

  • Theo Benedet, Chris Williams kick off Bears’ ‘Community Tuesdays’ at Conway Park Autumn Classic
  • Arabia Saudí firma un pacto de defensa mutua con Pakistán tras el ataque de Israel a Qatar
  • Asking Eric: Will he ever propose?
  • Bulls’ Josh Giddey extension has blatantly obvious future
  • Chicago Blackhawks Sign Wyatt Kaiser

Categories

Archives

Our Partners

All Sports

  • CHGO
  • Chicago Tribune
  • Chicago Sun-Times
  • 247 Sports
  • 670 The Score
  • Bleacher Report
  • Chicago Sports Nation
  • Da Windy City
  • NBC Sports Chicago
  • OurSports Central
  • Sports Mockery
  • The Sports Daily
  • The Sports Fan Journal
  • The Spun
  • USA Today
  • WGN 9

Baseball

  • MLB.com - Cubs
  • MLB.com - White Sox
  • Bleed Cubbie Blue
  • Cubbies Crib
  • Cubs Insider
  • Inside The White Sox
  • Last Word On Baseball - Cubs
  • Last Word On Baseball - White Sox
  • MLB Trade Rumors - Cubs
  • MLB Trade Rumors - White Sox
  • South Side Sox
  • Southside Showdown
  • Sox Machine
  • Sox Nerd
  • Sox On 35th

Basketball

  • NBA.com
  • Amico Hoops
  • Basketball Insiders
  • Blog A Bull
  • High Post Hoops
  • Hoops Hype
  • Hoops Rumors
  • Last Word On Pro Basketball
  • Pippen Ain't Easy
  • Pro Basketball Talk
  • Real GM

Football

  • Chicago Bears
  • Bears Gab
  • Bear Goggles On
  • Bears Wire
  • Da Bears Blog
  • Last Word On Pro Football
  • NFL Trade Rumors
  • Our Turf Football
  • Pro Football Focus
  • Pro Football Rumors
  • Pro Football Talk
  • Total Bears
  • Windy City Gridiron

Hockey

  • Blackhawk Up
  • Elite Prospects
  • Last Word On Hockey
  • My NHL Trade Rumors
  • Pro Hockey Rumors
  • Pro Hockey Talk
  • Second City Hockey
  • The Hockey Writers

Soccer

  • Hot Time In Old Town
  • Last Word On Soccer - Fire
  • Last Word On Soccer - Red Stars
  • MLS Multiplex

Colleges

  • Big East Coast Bias
  • Busting Brackets
  • College Football News
  • College Sports Madness
  • Inside NU
  • Inside The Irish
  • Last Word On College Football - Notre Dame
  • One Foot Down
  • Saturday Blitz
  • Slap The Sign
  • The Daily Northwestern
  • The Observer
  • UHND.com
  • Zags Blog

Copyright © 2025 · Magazine Pro on Genesis Framework · WordPress · Log in