
Struggle Session is a bonus column where I respond to comments. I also share a question submitted to Savage Love and let my readers have the first crack at giving the advice.
No Struggle Session today, as I am off this week. But while next week’s column is a repeat (because I am off this week), we’ve got a new Savage Lovecast and new After-Action Report for you. (So, while I may be off this week — have I mentioned that I am off this week? — I am not slacking.) But two points of order before we get to The Thursday Letter…
Point of Order #1: Dr. Jennie Young — author of Burn the Haystack and a recent guest on the Savage Lovecast — was kind enough to respond to a reader’s question in this month’s Quickies column. There was much more to Dr. Young’s response than I could fit in my monthly quick-and-dirty column. So here, as promised, is Dr. Young’s long, thoughtful, and generous response to this reader’s question…
13. Why do some men build consistent communication, emotional connection, and even physical chemistry with a woman only to suddenly withdraw or ghost instead of communicating where they stand? It just happened to me. This wasn’t a casual or surface-level interaction, and mutual interest was confirmed days before the switch so I’m trying to understand what typically causes that shift from a psychological or behavioral standpoint.
DR. JENNIE YOUNG: When this happens in early dating, I think it’s usually due to one of a few factors:
1. Emotional closeness and intimacy is truly uncomfortable for some people, even if they genuinely seek/want it. The psychological reasons for that are myriad and impossible to speculate upon out of context, and I don’t want to default to the overly-simplistic “he’s avoidantly attached!” response because that, too, is a multi-faceted and complex scenario; what I’m saying, though, is that I think there are cases in which things genuinely change or shift for people in a radical way that they may not want or understand but that is sort of beyond their control, at least at that point in time.
2. He connected with someone else or re-ignited a former love. I think this happens all the time in early dating. People get on the apps or “out there” in some other way as a response to something else going south, or out of boredom, or just for fun or whatever, and they “attach” quickly and immaturely to someone new, but in a way that it’s not really “real” for them and thus any distraction or former attachment that’s stronger due to history or new shiny object takes them out of it.
3. Something “happened” that triggered them or gave them the ick (I do not use this term lightly; I believe it’s a real and deep thing). It may be something you’d never even identify—you said something that reminded them of someone from their past, or they got freaked out by some potential glimpse of a future that scared them, etc.
In any case, here’s the upshot: what’s happened to you is incredibly painful, and incredibly common. It’s happened to me too. It’s tempting to engage in some post-game analysis that might go on forever, but the truth is that you don’t even have access to the details of that game, let alone its history, and it’s better to cut your losses and move on. I know that’s easier said than done, but it’s true. Try to sit through the discomfort of not knowing, and over time that discomfort will dissipate. It’s a wacky universe, and we’re just never going to have all the answers, to anything, unfortunately. I find that oddly comforting, and I hope that you might too. Be well. ❤️
Follow Dr. Young on Instagram @word_case_scenario (which just might be my favorite IG handle ever) and learn more about her work and order her book at her website.
Point of Order #2: EXCUSE ME WHAT?

OMG.
Alright, here is The Thursday Letter. Feel free to grab a beer and maybe order a pizza, dear readers, because it’s a long one…
I’ve been dating FWBs and focusing on myself a lot since a breakup of a on-year-long relationship over a year ago. (Slightly simplified timeline since I’m poly.) I’m writing because I’m struggling with whether my current partner and I are anatomically incompatible and need technical alternatives, if it’s an emotional issue, or both. For the record, I’m a bisexual woman that mostly dates and has only fucked men.
Last year, I’d have framed my problems solely as a demisexual. But I’ve come to learn my recipe is more complicated — because if someone is really my type and we connect over something deep in conversation, I’m flexible. This year I’ve had sizzling PIV fucking with a guy I first fucked three hours after meeting, but then I also had mind blowing fingering with a guy that I had a passionate but brief romantic connection with. (His fingering topped many PIV experiences I’ve had.) Both of those partners are no longer viable: the former tried obnoxiously to pressure me not to use condoms/irritated me with infrequent communication, the latter began to pressure me for a relationship I’m not ready for and then imploded.
I’ve had a new partner since late January. Our initiation to fucking was delayed a few weeks due to a bout of mycoplasma/BV on my part, and we developed genuinely fun and friendly emotional connection. He is also really hot, sexy voice, and totally my type. I did have concerns initially because he is a few inches shorter than me and described himself as having a small penis, but I found his penis to be pleasantly girthy and average, not small. Maybe just below average in the length department, maybe a little under 5″-5.5.” He is uncircumcised. When we initially started having sex, his dick actually felt too big or too painful, which I think may have been because of the dry spell I had when going through BV. After two times, I adjusted and found PIV with him to be snug and enjoyable, and I remember thinking what an amazing PIV experience it was for me in terms of shallow penetration sensation. PIV has been consistently pleasantly snug and massages my G spot, but when I’m on top of him and he makes a straight shot to my cervix it’s uncomfortable.
Flashback to my breakup. Unfortunately, my ex unlocked something in me in terms of PIV. I actually thought PIV with him would suck based on the first few times, but I think he had just been nervous and by 2-3 months, it was consistently good. Then it became insanely good; it was a guarantee he would pleasantly hit these spots deep inside me consistently without much effort. (Part of my theory on why he was comfortable acting shitty is that he knew women put up with his shit longer than they should because the pleasure he guaranteed them.) He was one of the longer dicks I’ve had, maybe 6″-7″? He was circumcised and while positions like doggy felt lackluster in terms of girth, pretty much every other position was good, missionary with my legs up was insane, and there was this one time I was on my side and he was entering me I clearly remember yelling how I’d never felt like that before. It was like he’d slid into a secret pocket that I was unaware of until that moment. It didn’t help that my ex was a lovebomber who made me feel like we were soulmates — and we fucking fucked like we were. Basically, my ex’s penis seemed to crawl up inside and around my deep vaginal spots like a demon and the pleasure still haunts me.
This week I opened up to my FWB about how I want to try hitting my “pocket” spot. Previously, even though he hinted he’d be open to using a sleeve, I didn’t want to talk about my desires because he had expressed his insecurity about his penis early on. This is highly emotional for me, because sex is the last thing I still put my ex on a pedestal for, and I know if someone else shares this kind of pleasure with me, his pedestal is no more. But it feels like a distinctly physical challenge, since my current FWB would need an additional inch or more more to get into that spot. After 2-3 months with my FWB where I felt like what I was getting is what I would get, I described how I had been experimenting with a dildo previously to recapture that P-spot feeling, and told him I want to explore it together with him. I will admit I cried a bit texting my FWB about it. My FWB turned out to be open to it, and we browsed a sex store together recently. He’s pretty GGG.
There are some considerations. I generally prefer not to use toys during sex because I don’t like distractions from our rhythm or my partner’s body, although I will try it. I also don’t know if he wears some kind of sleeve if it will make him girthier, which could actually make maneuvering deep inside me harder, as I find him girthy already. I’ve never used a dildo during sex. Neither of us have a ton of money to shell out on sex toys.
What do I do?
Sleeve first? Dildo first? A wedge pillow upgrade to my normal pillows? When do I call it quits?
My FWB is so great, and so fucking hot, and my fear is that if he was slightly insecure about his dick when he started, experimenting with a bunch of toys will diminish his confidence. Sex with him is great, it’s just not in line with this deep desire.
At the beginning of this year’s Slutventures, I talked openly on dates about wanting to queer the sex I have with straight men by talking more and relying less on PIV. So why is it that I’m so fixated on P spot stimulation, especially if I was able to be satisfied with fingering with another guy before? Are me and my shorter partner anatomically incompatible? Or is my vagina simply the last unrelenting bastion still attached to my ex, and she needs to accept that sexual experiences will vary? Or, wilder yet, am I too demisexual to have mind blowing sex with a friend and can’t unlock that next-level sex unless I have strong romantic feelings like I did for Mr. Lesbian Fingering? Can you help me make sense of this, Dan?
Please And Thank You
Got some advice for PATY? Drop it in the comments…