LIFESTYLE

When Your Dad Dates Your Best Friend: A Complicated Love Story

USATue Oct 21 2025

A 26-year-old is grappling with a strange situation. Their 56-year-old widowed dad started dating their childhood best friend, Corinne.

At first, it seemed innocent—coffee dates, shared laughter, and simple companionship. But now, six months later, the relationship is serious, and the family has been informed.

The writer is happy their dad found love again. But they also feel a strong sense of discomfort. The age gap is significant, and Corinne was once their best friend, making the situation even more complicated.

They want to handle this maturely but are unsure how to process their feelings.

Advice Received:

  • Accept the complicated feelings.
  • Everyone involved is an adult, so it's best to stay out of their relationship.
  • Corinne will likely move on to someone closer to her own age.
  • There's no need to worry about her becoming a stepmother.

A Mid-20s Employee Deals with a Potentially Alcoholic Boss

A person in their mid-20s is dealing with a boss who seems to be an alcoholic. The boss often invites young female co-workers out for drinks.

The employee doesn't want to be around their boss when alcohol is involved. They are hesitant to voice their discomfort because co-workers think the boss is funny and like that he pays for drinks.

Advice Given:

  • Send a letter to the appropriate people up the ladder.
  • Explain how alcohol is affecting the propriety and productivity of the office.
  • Stick to the facts and say you're concerned about having a supervisor who is sometimes impaired.

A Neighbor Asks a Family to Dress More Modestly

A married man with two teenage daughters is dealing with a neighbor who has asked them to dress more modestly. The neighbor's sons have been watching the daughters from a bedroom window.

The neighbor believes the daughters' clothing is too revealing and wants them to cover up more.

Advice Given:

  • Make it clear to the neighbor that being neighborly does not require leading his boys from temptation.
  • The neighbor is out of line for making clothing suggestions.

A Friend Reacts Harshly to a Question About Adoption

A person asked a friend's adopted child about the adoption in front of the child. The friends reacted harshly and changed the topic.

The next day, the person received an email from the friend saying they were out of line and wanted an apology. The person was unaware that the child had not been told about the adoption.

Advice Given:

  • Apologize, even if you don't feel you did anything wrong.
  • The friends are clearly sensitive about the topic, and your question caused them distress.

questions

    How do you think the daughter's feelings might change if she considers the potential long-term implications of her father's relationship with her former best friend?
    What are the potential benefits and drawbacks of the daughter accepting her father's relationship with Corinne without reservation?
    What strategies can the daughter employ to separate her personal feelings from the rational understanding that her father and Corinne are consenting adults?

actions