Admitting to using AI usually elicits one of two reactions: an enthusiastic “Isn’t technology great???” or a more skeptical eye-roll from someone who dreads a future resembling the once-fictional Her.
I used to be more like the latter until last Wednesday night, when my loud neighbors decided to host a rowdy get-together at 1 a.m. What I needed was a text message script—a kinder, more socially acceptable way of saying “Can you STFU” without making our next elevator run-in super awkward. So I turned to ChatGPT as a desperate, last-ditch effort. Long story short? No more late-night noise—and we’re still on great terms.
While there’s been plenty of chatter about all the ways AI could ruin our lives (and don’t worry, we’ll get into that), this surprisingly useful moment made me wonder: Well, what else could ChatGPT be good for? Sure, I wouldn’t expect an algorithm to solve nuanced existential questions about whether to end a long-term relationship or how to finally “fix” my seasonal depression. But when it comes to uncomfortable everyday conversations, maybe, just maybe, it’s got some potential.
So being the ever-curious journalist, I decided to throw a few of my own relationship dilemmas at ChatGPT to see what kind of advice it could offer. Then to get a sense of how solid those suggestions were, I tapped real, very qualified human therapists to evaluate them. And finally, we rated the ChatGPT’s answers on a scale of 1 to 10. Here’s where AI really showed promise in helping us navigate awkward, difficult scenarios with the right words—and where it fell short.
1. Telling a messy partner or roommate to be cleaner.
Question: How do I tell my partner I want them to be a little cleaner without nagging or micro-managing?
ChatGPT answer: Hey, can we talk about something real quick? I’ve been feeling a little overwhelmed by the mess lately—it’s not a huge thing, but it’s been kind of wearing on me. I totally get that we both have different thresholds for clutter, and I’m not expecting perfection at all. But it would mean a lot to me if we could both be a bit more mindful about keeping things tidier. I think it’d make the space feel a lot nicer for both of us.
Therapist says: This response isn’t terrible, Ciara Bogdanovic, LMFT, owner and founder at Sagebrush Psychotherapy in Los Angeles, tells SELF. It does a good job of acknowledging the other person’s perspective. “But it wasn’t done in a way that I think was very effective,” Bogdanovic says. For instance, the request to “be more mindful” is way too vague. “It’s difficult to get a result when you’re not being explicit and clear,” she says, suggesting you spell it out for them instead. Straight-up ask your SO to fold and put away the laundry, or make it clear you’d appreciate the dishes being done within, say, 24 hours. The more direct you are, the more likely you’ll see the change you’re hoping for.
Score: 6.5/10
2. Negotiating your rent in the most convincing and respectful way
Question: My landlord raised our rent, and I want to ask if there’s any way to lower it or at least keep it at the current price. What’s the best way to respond and ask for this?
ChatGPT answer: Hi [Landlord’s Name],
Thank you for the notice about the upcoming rent increase. I understand that costs are going up, but I wanted to reach out and see if there’s any flexibility in the new rate or a way to keep the rent at the current price.
I’ve really enjoyed living here and have tried to be a reliable and respectful tenant—always paying on time and taking good care of the property. If it’s possible to reconsider the increase or perhaps negotiate a smaller adjustment, I’d greatly appreciate it.
Please let me know if you’d be open to discussing options. I’d love to continue living here long-term if we can work something out. Thanks again for your time and understanding!
Therapist says: “I notice that ChatGPT seems to do the best in these middle ground interactions,” Ari Lakritz, PsyD, a clinical psychologist at OSF Healthcare in Alton, Illinois, tells SELF. “Those cordial relationships with people who aren’t really a close friend or family member.” ChatGPT’s answer here is respectful, assertive, and professional by our human therapists’ standards, but would be best received if you communicated it to your landlord over the phone or face-to-face. “People are generally more receptive and empathetic in person, slightly less so over the phone,” he adds. So maybe don’t copy and paste this into the body of an email.
Score: 9/10
3. Reaching out to a distant friend you’ve lost touch with
Question: I want to check in with a friend I’ve lost touch with. It’s been years, so it’s definitely out of the blue. What can I say that’s natural and not awkward?
ChatGPT answer: Hey, I know it’s been a long time, but you crossed my mind recently and I just wanted to say hi. I’ve been wondering how you’re doing and would love to catch up sometime if you’re up for it—no pressure at all, just thought I’d reach out. Hope things have been good on your end 🙂
Therapist says: According to Dr. Lakritz, this is one of those moments where AI still doesn’t quite nail how people actually talk. “This sounds really generic,” he says. Instead, “I would start with a shared memory or joke to personalize the message.” Think a quick, “Saw our favorite happy hour spot and thought of you,” or opening with a go-to meme. And don’t stop there: “I’d want to see some follow-up or a clear next step,” he adds. “Are you coming to their town and want to meet up? Do you want to set up time for a phone call?” That personal, nostalgic touch + clarity = a much better shot at actually reconnecting.
Score: 4/10
4. Voicing my feelings about being left out
Question: How do I tell a friend I wish they had invited me to their group hangout without inserting myself or seeming needy? Or is it best to not say anything?
ChatGPT answer: Whether or not to say something depends a bit on:
- How close you are to the person.
- Whether this was a one-time thing or part of a pattern.
- How much it’s actually bothering you.
If it’s just lingering enough that you’d like to clear the air, here’s a way to frame it that’s low-pressure and self-aware: “Hey, I saw you all hung out the other night—it looked like fun! I’d love to come next time if there’s room. No pressure, just miss seeing everyone!”
Therapist says: The advice is pretty solid, according to Jordan Conrad, PhD, LCSW, founder and clinical director of Madison Park Psychotherapy in New York City. It avoids jumping straight into blame or confrontation. But where a real, qualified therapist would shine is in helping you dig deeper into those feelings of exclusion or FOMO before rushing into the quick fix.
“A therapist wouldn’t just gear you towards an answer or a nice way to communicate,” Dr. Conrad tells SELF. “They’d want you to explore what exactly is bothering you about being left out”—whether it’s about this particular group dynamic or your own insecurities. That way, you can gain clarity on what you truly need in the long run, like a stronger sense of belonging…or a reality check about this so-called “friendship.”
Score: 7/10
5. Politely reminding someone who still hasn’t paid you back
Question: I feel uncomfortable asking someone to Venmo me for their part of the dinner, especially since it’s a friend’s friend (someone I’m not close