Each week, exclusively for Slate Plus members, Prudie discusses a new letter with a fellow Slate colleague. Have a question for Prudie? Submit it here.

Dear Prudence,

When should you go on a (probably?) date with someone you don’t think you’re interested in? I’m a 32-year-old cis woman who has identified as bi for a long time, but with a strong asexual streak. I’ve never had sex with another person or been in a romantic relationship, although I think I’d like to have a long-term partner eventually. Mostly, I haven’t been prioritizing this type of connection, there weren’t many people I was interested in, and the few crushes I had were hard to act on (for example, a teammate in college … but neither of us was out at the time). I have also spent the last 10 years in challenging recovery from anorexia, and that has made it really hard to socialize in general and to date specifically. I felt too messed up to be worth anyone else’s energy and worried that new partners would not be supportive of the weight gain I still needed to accomplish to be healthy. It is also possibly relevant that I’m neurodivergent and have a hard time picking up on social dynamics sometimes.

Two years ago, I moved to a new city for a university job and have since gotten to a significantly better place physically and mentally. I also happened to go to my college roommate (“K”)’s wedding and connect with another alum, “G.” G is very nice, we have quite a few shared interests, and I admire his zest for life, but he can also be a bit … intense. Since the wedding, he’s been inviting me to do various things both in group settings and one-on-one. I have mostly declined due to work and/or eating disorder struggles, so I’ve only seen him a few times in person since K’s wedding.

The last time was going on a small plane flight (he’s a pilot) with K and her husband. I had a good time, but he also made me kind of uncomfortable by presenting me with a variety of small gifts as a “thank you” for showing him around some campus facilities a few weeks prior. He’s since asked if I want to go to a museum with him, if I want to go to one of those murder mystery dinner party things (hosted at the museum, costing significantly more than I would want to spend on dinner), and if I want to go for a hike sometime. None of these were framed explicitly as a date, and they’re all things that, suggested by a generic friend, I would generally enjoy doing, but being faced with these particular invitations fills me with paralyzing anxiety.

My therapist is pushing me to give at least some of these outings with G a chance, with the reasoning that a big part of my resistance is fear of new situations, connections can take time to grow, and it would be a good learning experience. I am worried about encouraging his interest too much, given that I don’t think I like him the same way he likes me. Should I try doing more stuff with him and see how it goes? I’m lonely but I don’t think relationships are supposed to feel like this. How can I tell what internal signals I should listen to?

—Uncertain

Jenée Desmond-Harris: What is going on with therapists? This is reminding me of a conversation I had with a friend recently. She was telling me about a guy she’s been on a handful of dates with and all the things she doesn’t like about him—I think she even made a vomiting noise at one point to communicate how turned off she was—and then she said her therapist was making her give it three months. THREE MONTHS? I don’t have the credentials to disagree with any kind of authority, but I can’t get on board with that or with the advice of the therapist in this letter.

Nadira Goffe: Well, hold on—I think the letter writer needs to look inward for a second and really figure out if they like G or not, and the reasons why that may or may not be. “Intense” sounds a little strong. From reading, it seems like the only thing he’s really done is ask to do activities and … give gifts?

Jenée: But Nadira, come on! If she liked him she wouldn’t even be in this position because her only thought would be “I’m so excited, what should I wear to the escape room?” Right??

Nadira: I’m not entirely sure about that given the LW’s own admission of worrying about new partners in general. It’s entirely plausible that the LW does not like G! But it’s also entirely plausible that they’re scared to build that connection, maybe because it didn’t work out with their crush in the past or because they have these preconceived notions about the forms partnership can/should take. I know (from firsthand experience, maybe, but who is really to say) that when you’re out of the game for a long time, or if you’ve never been in the game, it can all feel scarier than exciting. But getting out of your comfort zone is scary!

Though, I will say that to me there’s an easy fix to all of this, which is to tell G that you like spending time with him (if that’s true? There was a lot of hemming and hawing about it!) but some of his actions are coming off as a little intense. And I think the best way to start that conversation is to absolutely ignore your therapist’s advice and say: Hey, G, are you asking me on dates? And go from there given his response.

Jenée Okay, this is fair. I can see that the letter writer is sort of uniquely out of touch with her own feelings. And I guess the therapist is trying to get her to have some dating experiences that will help to make it so that “I have never dated” doesn’t remain a big elephant in the room, making it even harder to date. I like the idea of asking him about his intentions.

But also … it sucks to be G! I don’t think I’d want someone feeling “meh” about me and accepting my invitations on a therapist’s orders!

Nadira: For sure! Being upfront seems like the most merciful thing to do in this scenario for both the letter writer and G. To your earlier point, if someone was leading me on for three months, I might resort to a life of violent crime. Plus, he seems like a nice enough person to still agree to be friends if LW says she doesn’t like him in the same way he might like her!

However, I do want to poke just another tiny hole in this letter, particularly in one of the final sentences: “I don’t think relationships are supposed to feel like this.” Honey, you are not in a relationship! Maybe in a platonic one, but not in a romantic one! I find this comment a little confusing because I’m not entirely sure what type of relationship LW thinks they’re in and what they think it should feel like. Rest assured if you were officially dating, I think it would feel very different. But that’s because when you define the relationship, you get to define what it looks like—what things you like and don’t like.

Jenée: And I would absolutely watch the Netflix doc and listen to the podcast about your dating disappointment-inspired crime spree.

I guess the letter writer did kind of address this, saying “I’m worried I’m encouraging his interest too much.” So maybe she can be honest. Not about all the details in this letter, but if he says “Yes I’m asking you on dates,” she could say something like “Okay! If that was a weird question it was probably because I’m not a big dater and I’m still figuring out how all of this works. But I’m flattered, and I’m definitely interested in the hike and getting to know each other a little more.” Just enough of a hint for him to know she’s not in a position to go all in.

My Friend Keeps Doing a Really Awful Thing in Front of Our Kids. I Need This to Stop. This Content is Available for Slate Plus members only I Have a $15 Million Estate and a Year Left to Live. My Son Is Going to Be Furious About My Plans for the Money. Help! I Can’t Believe the Very Strange Pet Names My Boyfriend and His Teen Girls Use for Each Other. I Work in the Business of Helping People Find Housing. One Colleague Is Absolutely Cold-Hearted About What We Do.

Nadira: LOL! So would I, to be fair. Netflix—call me! As for our dear letter writer, I think this is a perfectly worded response. And there’s also a way to tweak it to set even clearer boundaries if you’re sure that what you want is friendship and nothing more. But it starts, like most cases, with the letter writer figuring out what she wants and then figuring out how to get there. I don’t think going along without clarification for the exposure to dating or the experience is all that helpful if you don’t want to be more than friends. With that being said, if you didn’t care to know this person at all, I doubt you’d write this letter. The middle ground, if that’s what you want, is called friendship! And it’s totally achievable. It just takes a little bit of courage and clear communication.

Jenée: And a final thing that jumped out to me is that the letter writer says she’s lonely. So go on the dates with the goal of having company, not with the goal of deciding ASAP whether this will be your soulmate. As you feel less lonely, you might feel happier and better about yourself, and all of this could begin to feel a little lighter and more fun. Which is how it’s supposed to be!

So maybe your therapist has a point. I’ll retract my initial thought that you should get your copay back!