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The Worst Thing You Could Say to an Old Friend

Avoid this painful and oh-so-awkward pitfall if you're reconnecting with someone from your past.

The past seven months have had us all doing a lot of soul-searching. As you sat at home for days on end with little to do, you might have decided to reconnect with people who once meant a lot to you—a global pandemic will do that to you, after all. But reconnecting with an old friend can lead to a flood of emotions. It might even knock you off your guard enough to say something unintentionally awkward—or just plain hurtful. Of course, you know not to tell someone how much weight they've gained or to comment on their graying locks, but there are other, seemingly innocuous words you'd be prone to uttering in this situation that you simply shouldn't. So, what's the worst thing you could say to an old friend? "Remember the good old days?" Read on to find out why these words can wound, and for another time to choose your words carefully, check out This Is the Worst Thing You Could Say to Someone Who Lost Their Job.

It can be easy to assume that everyone in a group of friends remembers old times the same way—but that's not always the case. One person's great times could have been painful for another.

"Many of us may carry shame about our behaviors, decisions, and interactions, especially during our teen or young adult years in which we are still really figuring out who we are," says licensed professional counselor Leah Rockwell, founder of Rockwell Wellness Counseling.

Rockwell says you should instead "share a positive memory you have of them or a reminiscence about a former teacher or connection before allowing things to shift to the 'remember when' conversation."

She notes that if your old friend engages in that kind of chat, "you'll have gotten some good signals that this will be a heartening conversation, rather than one that is potentially more awkward for both of you."

Want more expert-backed tips on what not to say to an old friend? Read on, and for another situation in which you need to watch your words, check out This Is the Worst Thing You Could Say to Someone Who Just Got Divorced.

"I haven't heard from you in ages."

mother receiving phone call, etiquette mistakes

The fact of the matter is, people lose touch with one another all the time, and that's OK. Often, both parties are responsible for the drift, so placing the onus on the other person can be unfair and also uncomfortable. Beyond that, you just never know what people are going through.

"Calling an old friend is not an easy thing to do," says Sandra Glavan, the founder of Super Sensitive Sandi, a website for helping people reduce and manage anxiety. And that's especially true in our current era when anxiety is high. "Anxiety is the most common mental health issue in the world today. Dealing with an anxiety disorder can make you feel tired, overwhelmed, and anxious to do even the basic tasks in life," Glavan explains.

"Also, anxiety is characterized by excessive and irrational worrying," she adds. "People struggling with this mental condition tend to feel guilty for not spending time with people or calling them." And for more times to be careful with language, This Is the Worst Thing You Could Say to Someone Who's Grieving.

"Did you getting married?"

Man confused by text

The question of marriage can be "tone deaf and rude," says licensed psychotherapist Christine Scott-Hudson. "First of all, it assumes the other person wishes to get married. They may have just broken up with someone and are still in the throes of emotional pain. They may feel unlovable and worried that nobody will love them."

And there's a wide range of other possibilities, too. "They may be involved with someone who their family does not approve of, such as a same-sex partner, or someone who practices a different faith than the family's, or they may be polyamorous," she continues. "Just because someone is unmarried does not automatically follow that the person is not in a meaningful relationship… and the meaningful relationship might be with themselves." And for more major milestone advice you might need, check out The One Thing Everyone Should Know Before Turning 40.

"Do you have kids?"

Woman talking to family on phone call

Similarly, you might be tempted to ask your old friend about babies—but stop yourself. "Don't assume that this is just a casual and easy topic for people," Scott-Hudson says. "You have no idea what struggles and challenges people may have going on behind closed doors."

Perhaps they didn't want children, perhaps they have exhausted every fertility treatment available, or perhaps they've even lost a child. "Do not ask about this sensitive subject," Scott-Hudson says. "Just no." And for other questions to avoid at all costs, check out The Rudest Thing You Can Ask Someone, Etiquette Experts Say.

"What happened to you?"

young black man walking outdoors on video call
Shutterstock/SFIO CRACHO

When you talk to an old friend who seems worse for the wear, take pains to avoid letting on that you noticed. Offer help if appropriate or solicited, but don't just poke at the pain. "This question is tremendously damaging," says author and life coach Aidan Park. "It implies there is something wrong with an old friend. It's best to establish some type of safety in the connection."

He adds that "any statement that triggers a feeling of judgement or that something is wrong with them has a counter effect in creating a safe environment." And for more helpful tips delivered to your inbox, sign up for our daily newsletter.

Alesandra Dubin
Alesandra Dubin is a lifestyle editor and writer based in Los Angeles. Read more
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