Dear Prudence

Dear Prudence Uncensored: Single and Silent

Every week, Danny M. Lavery and Nicole Cliffe discuss a Prudie letter. This week: single and silent.

Nicole Cliffe: It’s definitely not her (very normal) height! She just needs to get out there more aggressively.

Ask for set-ups SPECIFICALLY

Start doing those classes people do to meet people, like cooking and what have you

Daniel Lavery: yeah I think your friends and family members are being polite by not saying anything because *you* haven’t said anything

Nicole Cliffe: They’re being super polite!

Daniel Lavery: and they know that it’s rude to ask intrusive questions about someone’s personal life when they haven’t volunteered any information

so it doesn’t mean they don’t care or they think of you as somehow uniquely unlike the rest of humanity

Nicole Cliffe: Go ahead and volunteer that you want a partner!!

Daniel Lavery: they’re truly just respecting your privacy, which is a good thing, and if you actually want to discuss it with them, you have to be the one who lets them know

and obviously you can do that and still set boundaries

it doesn’t mean you need to declare open season on “why” they think you’re single

but I think that’s contributing to a lot of this sense of isolation, that you haven’t talked about this with ANYONE

Nicole Cliffe: Also, try a different app and try to figure out what specifically makes you uncomfortable

Daniel Lavery: and also means you’re just left to come up with random theories like “maybe no one likes 5’11 women”

I agree that asking to be set up is a good first move but it’s 2020 and if you’re not going to be on the apps at all, you’re going to limit your options

Nicole Cliffe: Because that might very well carry over to non-app first dates as well

Daniel Lavery: and of course some of it is just that apps are full of STRANGERS

and you don’t immediately feel chemistry or interest in a series of pictures and jokes about hiking

Nicole Cliffe: My husband was too early for the apps and he had to take a singles tango class, you should be grateful for the apps

Daniel Lavery: but it’s also good practice for figuring out what you like, what you don’t like, how to flirt, how to express interest, how to handle rejection, etc

Nicole Cliffe: Yes!! Practice your “getting-to-know-someone” material

Daniel Lavery: so even if you don’t end up meeting many people from the apps it can help to make dating seem less mystifying and like everyone else got a booklet explaining the process in 9th grade while you were in the bathroom and missed out

Nicole Cliffe: This is why people do fake job interviews with their friends

Daniel Lavery: I haven’t had any serious relationships come from apps, but I’ve used them at various points in my dating life, and I often found them at the very least entertaining, sometimes fun, sometimes a drag

Nicole Cliffe: Be like “this isn’t real, so there’s no reason for me to feel weird,” and then maybe you’ll find something real or just use the lessons on an actual set-up

Daniel Lavery: not to be all “Well, I’m a weird height and I’m married, so I obviously have all the answers to dating,” but I am a 5’7 transsexual and I do okay – of course there are various weirdnesses that shorter men and taller women face, especially in heterosexual dating, but it doesn’t disqualify you from dating at all

Nicole Cliffe: Your wife is as tall as God

Daniel Lavery: there are many lids in the world, even if not necessarily for every single pot

she’s 5’11!

Nicole Cliffe: She’s glorious. I am profoundly attracted to Elizabeth Debicki and she’s 6’3, lots of people love tall chicks

Daniel Lavery: it will really help to stop framing this as “Every man who has ever met me has considered asking me out and then decided against it”

Nicole Cliffe: Just know: it’s not that you’re too tall to date


Daniel Lavery: you have no way of knowing how many people have almost asked you out, or wanted to but were themselves shy and uncertain, etc

Nicole Cliffe: Ask THEM out

A lot of guys love that

Daniel Lavery: when you don’t know what’s going on in other people’s heads it’s easy to assume they’re all making clear, informed decisions and doing everything on purpose

yeah, I really don’t have a better answer than “talk to your friends and family, ask people out who you think are cute, practice flirting in low-stakes scenarios until you feel less stilted doing it”

Nicole Cliffe: Did I tell you about the time I misread a situation completely and still got a date out of it

Daniel Lavery: if you just try to make yourself seem “Generally Ask-Out-Able” and keep hoping someone’s going to do it, you’re going to experience a lot of unnecessary frustration

and that also means gearing yourself up to hear “No” and not seeing it as further evidence that you’re undateable, just part of the process of asking people out. It’s built in! if you ask people out, some of them WILL say no, and you can handle it, I promise, even if it brings up fears of rejection at first


Nicole Cliffe: I was at some political fundraiser, on a maybe-a-date.

I’m pretty confident that if a guy picks you up and takes you to a political fundraiser and gets you wine, it’s a date.

Daniel Lavery: I have no objection to this assertion

Nicole Cliffe: Good. This was NOT the misreading.

So I’m wearing a cute dress

And there’s this guy with red hair who is very funny and engaging (and shorter than me, by the way)

And I think we’re definitely vibing

So at the end of the night, I decide to make my killer move

Which was to pull him aside and whisper in his ear “look, I came here with someone else so it would be rude to go home with you tonight, but here’s my number”

Daniel Lavery: Charming!!!

Nicole Cliffe: I thought so!!

And he looked BAFFLED

and said the first thing that came into his head

Which was “I had not thought of asking you out at all”

Daniel Lavery: And yet here you are, alive today!

Nicole Cliffe: But he took the number


Nicole Cliffe: I had PRESSED IT INTO HIS HAND while making my move!! He already had it!

And then he called me two days later and we went on three dates.

Daniel Lavery: I did not see this coming

so he WAS charmed by it, and just got flustered and said something stupid?

or he just offered the three dates out of respect for your spiritual courage?

Nicole Cliffe: I think he just dug/appreciated the move.

But the dates were good and I found him very attractive and then his ex moved back into town and they got back together

Daniel Lavery: and it’s fine! no one died!

Nicole Cliffe: NO ONE

Daniel Lavery: I really think the goal here should be to just get PRACTICE asking guys out and going on dates

Nicole Cliffe: you gotta take some risks

Daniel Lavery: which is not to say you should ask out every guy you meet, or go on dates with someone who completely turns you off

Nicole Cliffe: Absolutely not

Daniel Lavery: but once you start to think of asking people out as something you can do, and the possibility of getting turned down not as some soul-crushing indictment of your lovability but merely a natural part of dating

Nicole Cliffe: but if you feel a vibe, be open to making a move


Daniel Lavery: it’s going to feel a lot less like “relationships happen to other people by natural magnetism and I’m the only one it doesn’t ‘work’ for”

Nicole Cliffe: And also don’t put too much pressure on the first person you actually go on a date with, like they will be your life partner

Daniel Lavery: also, you really do seem lovely

and I hope that talking about this makes you feel less lonely

Nicole Cliffe: Yes!!

I like her too

Daniel Lavery: you might enjoy reading Katie Heaney’s “Never Have I Ever”

Nicole Cliffe: is this a roundabout way of saying “have you considered lesbianism” because her next book was about falling in love with a woman

Daniel Lavery: Truly, no!

Daniel Lavery: I just think it might feel nice to read a book from someone who felt something similar in her 20s

Nicole Cliffe: Also, ask all your partnered friends how they met

Daniel Lavery: there are so many different possible futures from a place of “something about heterosexuality isn’t quite clicking for me right now and I can’t quite put my finger on it”

Nicole Cliffe: People love to talk about it

and you may discover avenues that are new to you!

Daniel Lavery: and it doesn’t retroactively erase the experiences Heaney talks about in her first book that she later came out

Nicole Cliffe: Oh, absolutely. It’s a great book.

I really hope we helped this woman today!

Daniel Lavery: I do too! Good luck!