Every now and then, I chat US politics via DM with @SarahCantSmell, a dating blogger and academic from somewhere along the East Coast. In the run-up to the September midterm primary elections, we struck a bet on the outcome of one high-profile race. I was pretty confident of victory, tbh, and as someone who’s always enjoyed Sarah’s writing – and thoughtful perspective on love, sex and dating – I knew exactly what I wanted as a prize…
A few weeks ago, I came out on the wrong side of a politics-related bet to EA. We’d agreed that if I lost I had to write a guest post for his blog, from a shortlist of prompts and topic ideas. (If he’d lost, he’d have had to make a video explaining the British system of government for my political science students, something I am still hoping to finagle out of him or some other Twitter friend at some point.)
One of the suggestions he gave was that I “respond” to one of his previous posts; among them was this post about sexting. It immediately caught my attention because I feel like this is an often-debated topic, and is one of the few dating-related topics that I feel both single people and those in relationships can weigh in on equally, as sexting can still be a common activity in a relationship. People tend to have wildly different opinions on it; even within EA’s post, he mentions a Medium article by Lucy Goes Dating. He notes:
“Among her 15 tips for being a better man while dating – many of which are perfectly solid nuggets of wisdom (‘Only swipe right if you’re actually interested’, ‘Don’t brag’, ‘Be kind and considerate’) – was this little eyebrow-raiser: ‘don’t mention sex AT ALL before you meet’.”
He goes on to try to refute that idea, and while I think he makes really solid points, I personally lean more to Lucy’s side of things. I think EA makes great points about how even if you meet and there isn’t chemistry in person, you still could have had an enjoyable time sexting, so it’s not as though it was all for naught. However, maybe his and my views on this issue just differ a bit, or maybe it is because I am a woman and I have to consider my physical safety before a first date more than a man does, but I personally am hesitant to get myself into a situation where there are such clear expectations of sex before a first date. Even if I enjoyed the pre-date sexting, I would not be confident that a man would accept my view that there was no in-person chemistry and just happily leave me alone to go our separate ways after the date. In my opinion, women can set themselves up for harassment or worse if they sext before a date and then decide they are no longer interested after meeting in person. It’s no secret that many men don’t handle rejection well and I would be afraid this would add to that problem, so I tend to avoid it pre-first date.
Obviously, this is entirely situational, and there may be times where both parties feel comfortable with it, and in that case, go for it! I am all for everyone doing whatever makes them happy. But generally, I steer clear before a first date and many of my female friends feel the same. So with that in mind, I am going to focus on a more specific time frame for this post: the time where you have met in person, had a date or two already, but have not actually had sex yet. In my opinion, this is a very precarious time for sexting. It can really help build up anticipation and excitement, but if done wrong it can also come off really creepy or inappropriate. I’m going to offer a few tips for men on how to successfully sext during this early time, before you know a whole lot about a person’s sexual preferences (or really a whole lot about the person in general).
Before I move on to the advice, however, full disclosure: I am awful at sexting. I had a humorous situation a few months ago where I jokingly tweeted that I needed a “friends with benefits” so I could practice sexting without fear of being judged or scaring away a new man that I actually wanted to date. A Twitter friend didn’t recognize it as just a funny way to mock myself, and thought I was really asking, and she RTed it in an effort to find me strangers to sext with. I received quite a few interesting DMs that day!
Me being horrible at sexting really doesn’t make a lot of sense. For one thing, I am good with my words in other ways. For another thing, growing up, sex was a pretty open topic of discussion in my house, at least between me and my mom. From a very young age, she imparted the wisdom that waiting until marriage to have sex is a really bad idea. She explained that sexual compatibility is very important in a relationship and waiting until you’ve made a lifetime commitment to someone to make sure that compatibility is there is not doing anyone any favors. When I eventually lost my virginity as a teenager to my boyfriend at the time, I would talk to her about our sex, about things I liked and disliked about it, and she would even make suggestions for positions to try or ways I might enjoy it more. I didn’t realize at the time just how rare this kind of parent-child dynamic is during your teenage years. But looking back, I am grateful for it. Sex was not taboo in my house, and making sure I got pleasure from it was always at the forefront of our discussions. As I have gotten older, it has saddened me to realize how many women did not grow up with the idea of their pleasure being so centered into discussions about sex.
In my experience, people who were brought up with this open attitude toward sex are normally more naturally suited for activities like sexting, but for some reason, I am awful at it. Part of that might be due to the fact that until the past couple of years of being single, I didn’t really have a strong need for it. In my early 20s, I mostly went on dates with people I met “IRL.” There wasn’t a whole lot of flirty text build up, because we had done that in person. I tried a couple of dating sites and went on a few dates from them, but I really wasn’t heavily engaged in the online dating scene. Right around the time I got a smartphone, which in a lot of ways makes sexting easier and more fun, I started a long relationship with someone who had previously been a friend and later a friend with benefits. Because of our extended transition from friendship, we sort of skipped any heavy sexting phase. There was some flirting prior to entering our relationship, and a few pictures exchanged early on, but for the most part we just didn’t have the type of build-up with which sexting usually coincides. But now here I am in the world of dating apps and “modern dating,” and sexting sometimes has more of a place in my life than it did before (hence my Twitter joke that I need to get better at it).
I say all this to make clear that I am by no means an expert on sexting. This is advice and a few tips for men that I have gathered from my own experience (however cringeworthy that experience may be) as well as the experience of some close friends. It’s worth noting that this is specifically aimed at male/female dating dynamics because I am a woman who has only ever dated men. Some of this advice is universal but other parts apply specifically to heterosexual relationship dynamics because that is the only perspective I can offer. Lastly, I’d like to think a lot of this is common sense, but I still see men regularly getting it wrong, so I thought these things were still worth mentioning.
Without further ado, some tips for men who want to sext women that they have met but have not yet had sex with:
- Let the woman lead, at least at first…
This doesn’t mean you have to let her lead the entire conversation. It doesn’t mean you can’t talk about things you want to do, and it doesn’t mean you have to assume the more “submissive” role in the conversation if that is the dynamic you’re going for. But it means you shouldn’t let a conversation even get to a sexting level unless you are 99.9999% sure she wants it to go there. (You can never be totally sure until it is happening, but you should be as close to 100% as possible). Dip your toes in with some flirty comments, and see where she takes it. When you have met a woman and have plans to hang out again, it is clear she is interested in you at least to an extent. But different people have different tolerances for how much they’d like to talk about sex prior to having sex, so don’t jump right in and risk making her not want to talk to you anymore.
- …and definitely let her lead when it comes to sending pictures.
Personally, I think sexting is better without pictures. I think pictures have their place in sexual conversations, but, at least for me personally, the way I would make use of a consensual, requested dick pic is different to the way I’d make use of an immediate, in the moment, back-and-forth sexting conversation. The former is something I may want to have in my phone to look at when I want to, when I am thinking about someone, but the latter is something I want in this moment, to build upon whatever conversation or fantasy we are discussing right now. If I am sexting back and forth with someone using mostly words, and then I get a sudden dick pic, to me it feels abrupt and kind of ruins the moment. Cool…now I have a photo of your dick. Thanks for that…I guess…? But now my mind is processing the photo, rather than focusing on the conversation we were just having. I would advise men to not send pictures unless she A) specifically asks for one or B) sends her own pictures first. Even with B, it is still a good idea to warn her that a photo is coming her way. Women are inundated with unsolicited dick pics on a regular basis. Even in a sexting conversation, a bit of warning is appreciated. Plenty of women like exchanging photos and see it as a key part of sexting, but until you know what they prefer, I think it is safer to lean more on words. Being abruptly asked for a photo or randomly sent one is a turn-off for a lot of women.
- If you do get to the photo-exchange stage, for the love of god do not save her photos.
Women have a lot to fear these days when it comes to exchanging photos. There are so many stories of people getting their iCloud hacked, or men posting “revenge porn” online. If she is sending you photos at all, even photos where her face isn’t visible, she is establishing that she at least has a basic level of trust in you. Do not fuck that up! If she texts it to you directly, then I guess you can save at your discretion unbeknownst to her. But if it gets sent to you over Snapchat or Instagram or some other way, leave it within those channels! A friend had an issue recently where a guy saved and screenshotted some photos from Snapchat (even after she had specifically asked him not to), and she got a notification about it. It completely ruined the fun, flirty, sexy dynamic that had been built and made her lose all trust in him.
- Establish consent throughout the conversation.*
Just as with real sex, you should be establishing consent at various stages of a sexting conversation. This not only serves to make sure the woman is comfortable with what is happening and likes the direction things are moving, it also gives her a chance to express some of her own desires. If you are doing the type of sexting that is more just telling people things you enjoy, fantasize about, etc., you can establish this type of consent by saying things like “Do you want to hear more?” and you can invite them to share some of their own thoughts by saying things like “Have you ever thought about stuff like that?” If you are doing the type of sexting that is more like real-time commentary e.g. “I am doing XYZ to you,” you can establish consent in a similar way that you would in real life, by saying things like “Do you want me to keep going?” or “Are you enjoying that?” This gives her the chance to say things like “Yes, keep going, but tell me more about _______” or “Yes but tell me what you would do if I ________.” Consent is important in any sexual activity, but in sexting, it can also really enhance the conversation and therefore YOUR experience.*Women, of course, should also be continually establishing consent. Obviously there can be situations where the woman wants to say or do more than the man or the man is just outright uncomfortable. But this advice is specifically geared toward men who want to sext, so that is the perspective this advice is coming from.
- Don’t assume that just because a woman doesn’t want to sext with you, or doesn’t want to get that deep into sexting, that she isn’t sexual or doesn’t want to have sex with you.
A lot of men seem to make the mental leap that just because a woman doesn’t want to engage in something like sexting, they must not want to have sex with them. And this is often extremely untrue. While I think there are definitely arguments to be made for sexting prior to having sex, some people prefer to do it the other way round. For me personally, I am not necessarily against sexting prior to sleeping with someone, but I do find it much easier after I have slept with a guy, as I can reference things he liked in bed or things I know to be true about him or about our sexual dynamic. Since I am not very good at sexting, having this real experience to weave into the conversation is very helpful to me. Some people just prefer an in-person build up and don’t get much out of sexting prior to having actually slept with someone. Other people are just not big fans of sexting in general. While I understand it can be a bit of a shot to your confidence if you try to put yourself out there in flirting or sexy texts and you don’t get a lot in return, you could be missing out on a really good thing if you automatically assume that because a woman doesn’t want to do this with you, they aren’t interested in you at all, especially if you haven’t had sex yet. Once you have had sex, if things like sexting are important to you in terms of keeping the momentum going and she still doesn’t really seem interested in engaging in this type of activity with you, then maybe you just aren’t compatible in a dating sense. It doesn’t make either of you right or wrong, it just makes you not a good fit. But, a little bit of patience prior to having sex can go a long way in this area.
Sexting is something that can be fun and exciting if both parties are into it. But when done wrong, or when pushed too hard, it can ruin the buildup and keep you from ever getting to ACTUALLY have sex. While sexting can be enjoyable, in my opinion it should be engaged in carefully before you’ve slept with someone – otherwise you may sabotage your own chances of going any further. My hope is that by following these tips, men can help ensure that pre-sex sexting is a nice build-up and complement to sex, and doesn’t end up making the woman so uncomfortable that you never end up getting to that point.
I’d like to thank Sarah for being such a good sport, and for providing some genuinely insightful sexting tips and tricks. If you want to read more of Sarah’s work, do make sure you check out her Medium page and follow her on Twitter.
