Mailbag #4 – Sex, Dating Apps, and The Burned Haystack Method

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Thanks for all the amazing questions in this month’s mailbag. I’ve posted them below. You can watch the full video where I answer them all by subscribing on Lovesplaining.


How many times should we write back and forth on a dating app before the guy asks for a phone number? It seems like some of these guys want to be pen pals.


Ready for Lasting Love?
Ready for Lasting Love?

If you’re going through a big change like starting a new job, having a health procedure, etc. would it be wise to hold off on dating until you’re settled? Or does it depend and if so, is there a different way one should approach dating if going through things like this to set expectations? When is the right time to have that kind of conversation?

Carrie R

When is it a good idea (or at least not a bad idea) to get back with an ex- boyfriend? Especially if neither party cheated. If you do date again at what point should the “what are we doing” conversation happen? Should women wait for the man to bring it up or should we?


I am 40, healthy and fit, and have just frozen a few very good quality eggs after a medically smooth but really stressful process. If I was dating someone a bit more seriously, should I bring this up and tell him? I am very mindful of not interrogating a man or putting pressure on him – as a matter of fact, I’ve suffered from the very opposite of that my whole life. But I don’t want men to think I am worthless as a wife and future mother of their children because I am 41 or 42. I need them to know I have very good chances.

Annie M

Something I run into is having a good exchange on an app, exchanging numbers, setting up a date, and then it’s crickets from their end once the date is set up. No further communication or attempt at connection/getting to know me until the date. I get why people do this but it kind of kills the connection for me. Should I be more open to meeting a guy when this happens, or am I right to be turned off by this?


When does a player realize he wants a serious relationship? Or do they never have one because that’s the point of being a player?


I have a question about “testing the goods” BEFORE making him my boyfriend. I agree with your advice to not sleep with him until he’s my boyfriend if I want a relationship. This has been my experience too. However, I have been finding myself in unsatisfactory sexual relationships, and then feeling shallow for being dissatisfied, when he’s such a great guy otherwise and now I’ve already made him a boyfriend. For example, erectile dysfunction, very small penises, premature ejaculators, 50-year-old men who have sex with the sophistication of a teenager, etc… I’m comfortable expressing my needs and evolving with someone, but some of these things are beyond that. Yes, I could end it then, but that seems so cruel. How do women get around this dilemma?


Estela G.

Where should women meet good quality men outside apps? Is following our own interests enough?


I would like an official EMK opinion about the Burned Haystack Online Dating Method. See Jennie Young Instagram. I found it to be extremely refreshing.


I’ve seen a lot on social media lately about attachment styles. Is this something that a mental health professional needs to diagnose? From your experience and observations, how self-aware are men and women about their attachment styles and their willingness to address or improve any attachment issues?

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