How Do I Make the Leap From “Friendly” To “Flirting”?

Hi Doctor,

I’m (28M) writing to you to ask about an issue that I have had for a while in dating that I’m struggling to figure out how to tackle. I’ve been single for quite a while and have just been casually dating, which has been great for me. I mostly meet people on apps and go from there. I’m not the world’s biggest player, but I feel like I do okay, the only issue I have is with establishing a sexual/romantic connection.

A lot of my dates end with the other person saying that they had a nice time but didn’t feel a romantic connection. Which is totally fine. I’m not a “nice guy” or someone who is going to complain about the “Friend zone”. If I got to have a few drinks and some good conversation with someone and that was all it was, I’m not going to feel upset about that. But at the same time, that isn’t the reason that I’m on these apps.

Obviously attraction plays a big part of it, especially meeting through apps it is something that is hard to gauge before the date and also something that I don’t have much control over. But I feel like I have a pretty good idea of what is holding me back, at least in terms of things I can control.

I have no idea how to initiate anything.

Most times that I do hook up with someone on a date, they have been the one to initiate it. This doesn’t even just apply to my casual dating life. Almost all of my relationships, long-term and short-term, even back through my teen years, were initiated by the girl. As a result I really feel like I don’t know how to pivot things into the direction that I want them to go.

Socialising and conversing is not something that came easy to me and has been a struggle for a long time, but I have put a lot of work into it over the last 5 years and I feel confident and less anxious about talking to people now. The only issue being that I don’t know how to move past friendly conversation into a more flirty or suggestive vibe.

I think this may be where I am losing people on dates. We can have a great conversation over the course of the date, but unless they are actively wanting to hook up and steer things in that direction, then we remain stuck in friendly conversation until the date ends, and they end up not feeling anything other than a friendly connection.

I don’t have any interest in using any kind of pick up techniques to trick or convince people to hook up with me. I just want to increase my ability to elevate the connection with people who would be interested in me.

Can you help me figure out how to move things from friendly to flirty?

FriendZone Vibers

It’s good that you can tell where the disconnect is, FZV; a lot of folks who struggle with similar issues don’t know what the issue may be, just that something’s wrong. So, the fact that you have a solid idea of where things are going wrong is a huge plus.

But it also means that you know the solution too. It’s just a matter of executing on it.

Let me explain. We hear all the time from guys who are trying to meet women or who are out on dates with women they have met, but never feel sure that those women are interested in them or not. They spend most of their time worried about how those women feel and try to read meaning into every little vocal inflection or word choice like they’re trying to find the secret resting place of the Holy Grail. What we often don’t recognize is how often women feel the exact same way. Yeah, you can make the obvious (hacky, boring, inaccurate and overdone) jokes about “guys are always horny” or “men are always looking for sex so assume they’re into you”, but the truth is that women are just as nervous and unsure as men are.

I mean, shit, there’re how many books out there about how to ‘read’ men and know if they like you or not?

Of course, this mutual sense of “wait, I’m not sure…” leads to a very common response: it’s safer – or at least, less  potentially embarrassing –  to assume friendship or disinterest. If you’re not picking up obvious flirting signals from someone, then it probably means that they just see you as a friend… right?

And to be sure: yeah, it’s more likely. But there are plenty of times when the real issue is that the other person was too nervous to make their interest more overt. So it’s not that they’re not interested, it’s that they’re afraid to make it clear that they’re interested too. For a lot of guys,  there’s the understandable worry that flirting or signaling interest is going to screw things up… somehow. Maybe they misread the situation first and their “date” thinks this is an outing as friends. Or they worry that being obvious with their interest will be creepy or unwanted. Hell, sometimes guys think that showing interest is a bad thing and means you’ve lost the upper hand in the interaction because of “who cares less, wins” psychological bullshit.

Needless to say: this is a great way to enjoy a lifetime supply of singledom. The fact of the matter is, as with most things in life: if you want something, you need to be willing to go for it. Sometimes this means asking for what you need instead of hoping that other folks will somehow divine your needs for you. Other times it means being willing to show someone that you’re interested in them, in a clear and unmistakable way.

And yes, the “unmistakable” part is important. People will often miss even what you would think are the most blatant invitations possible. I still remember a young woman in college who told me about how she had this Japanese animated horror movie she wanted to watch but she just was too chicken to watch scary movies by herself…

It took me years before I realized she was asking me to come back to her dorm room for a hot cup of “fuck my brains out.”

Anyway, the point is: you need to express interest in the women you go on dates with, FZV. And you need to express that interest in a way that says “I like you as a potential romantic or sexual partner, not a platonic friend.” But you already know this… you just aren’t doing it. You’re clearly letting other people drive the interaction and oh look it’s not working out for you because they think you’re not interested.

Flirting is the most obvious way of demonstrating that interest in a playful and fun manner, and there’s any number of ways to flirt. Flirting is, at it’s core, just a way of telling someone you like them and inviting them to reciprocate. But  you’re not doing this. So the big question here is: what’s stopping you from flirting?

The most likely answer is that you’re worried that your flirting or showing overt interest might be unwanted or unwelcome. This is a common dilemma for a lot of men, especially men who’ve struggled with dating and who’ve made improvements in other areas of their lives. While they may have tackled the other aspects of their personal development – cultivating their style, working on their grooming and presentation, living an interesting life,etc. – they still have those brainweasels that insist that women would find their romantic or sexual interest to be unwelcome at best or outright insulting at worst.

And while I absolutely can understand that particular anxiety, in your case, FZV, you’re on dates with these women. As a general rule, people don’t go on dates  – clear, unambiguous dates – with people they’re not at least a little interested in. That’s the whole point of a date; they’re interested enough to see if there’s mutual attraction, chemistry and compatibility. So, honestly, you’re on safe ground there; if they’re on a date with you, you can take it as a given that they’re ok with your being interested in them. So why not let them know?

Now an response to that question would be: so… when do you start flirting? When do you move the conversation from “friendly” to “flirty”? And the answer is: “what do you mean ‘start’?” If you’re on a date with someone, you don’t necessarily shift gears like a business lunch, moving from pleasantries to the business at hand. You don’t wait until midway through to start showing interest… you can start flirting from the moment you meet up with them. It’s not about making a shift so much as keeping up a low level of flirting that you can ease into and away from as needed.

Think of it like this: if the point of a date is to gauge mutual chemistry and compatibility, flirting is both a way of building and measuring attraction. It serves both as letting someone know how you feel, creating an atmosphere of collaborative play (for lack of a better term) and pinging for where they are. You do this by using different levels of overt flirting and seeing how they respond. Just as there are many different ways to flirt, there’re different levels of intensity to flirting. Think of it as the many levels of difference between “I think you’re incredibly cute” and “I want to take you back home and part you like the Red Sea…”

By having that low background hum of flirtation from the jump, you create an atmosphere where interest is both demonstrated and acknowledged, and that you can dial up or down as the situation warrants. At the start, you want to keep things relatively light – appreciative and interested, but not crass or overly sexual (assuming that this didn’t start from a sexual place when you were planning the date). So, as an example: start the date with a compliment. Whether you’re meeting them at the location or you’re picking them up (or they’re picking you up), one of the first things out of your mouth should be a sincere “wow, you look amazing!” This serves a dual purpose. First: people do put an effort in to look nice before going on a date; complimenting and appreciating that effort is always a good thing. Just as importantly, you’re showing that you like what you see and paying them a compliment on their effort. You’re creating that sense of “Ok, I definitely like you, let’s see if we have what it takes to make this work.”

Having created that baseline of interest – hopefully mutual interest – you have set the tone for the interaction and put flirting on the table as you get to know each other. This means that you can dip back into being flirty as the occasion warrants, and dip back out again, without feeling like you need to shift into “time to flirt” mode. So as you’re asking her questions about herself (and you are asking questions, not just talking about yourself, right?), you have an opportunity to pay another compliment: “your eyes light up when you talk about $FAVORITE_THING in the most incredible way” for example or “you do $INTERESTING_THING? That’s so cool!” or “wow, nobody’s made that make sense to me before, that’s amazing.”

Paying sincere compliments, especially ones that validate or affirm them for being cool, interesting, smart or other non-physical qualities, is a great, low-key way of flirting. It makes the person you’re complimenting feel good and validated, especially when it’s something they clearly care about. Making someone feel good, incidentally, is one of the ways we encourage people to like us – it’s the Reward Theory of Attraction in action.

Now, it is important to remember that while you don’t want to go sexual early on without a clear vibe from the start,  you do want to also do a little sexy flirting as well – at least enough to let them know you’re interested in them physically as well as mentally and emotionally. After all, we’re not just people, we’re also pieces of meat. But that doesn’t mean being gross or crude. Giving a light tease, a playful “misunderstanding” or innuendo that takes things in a slightly more sexual direction – pretending that you thought they were making some sort of come-on – is a way of adding a sexual vibe to the flirting without making things uncomfortable. To be sure: this requires a light hand and should be used sparingly at the start. Few things are more tedious or obnoxious than someone who keeps turning the conversation in sexual directions. Used sparingly and lightly, however, these moments can be both funny and creates an opportunity for them to flirt back.

In fact, giving those opportunities to flirt back are ways of pinging their interest level. If, for example, she says something that could be taken in a couple of ways, you respond with a teasing “I like it but I don’t know if that’s appropriate just now…” and she acts confused or doesn’t flirt back, then you know she either doesn’t get the joke or isn’t necessarily feeling that level of interest just yet (or both). That’s a sign to dial back the flirting a bit and maybe take it back to non-sexual flirting and bantering.

On the other hand, if she replies with “Oh but why not?” or escalates the joke, then you’ve got a pretty good indication that she’s feeling the physical attraction too. She’s not saying “take me now in a manly fashion,” but she is playing along, which is a good sign for you. You can continue the bantering back and forth and then break that moment to be more serious for a bit. Then, a little later on, you can flirt some more.

In fact, this flirt/break rapport/flirt pattern works well for building attraction. It’s building tension, then releasing the tension, and then building it again. That pattern of build/release is vital for proper flirting. A lot of people think that the key to building attraction and chemistry is to just keep building tension until the other person explodes into a cloud of lust. In reality… that’s actually not great. It gets uncomfortable pretty quickly, even with someone who’s into you. Instead, think of building and releasing tension like a roller-coaster. Coasters aren’t all just OK NOTHING BUT DROPS AND LOOPS; there’s the build-up (ratcheting to the first drop) then the release (the initial drop), moments where things slow down for just a second to let folks catch their breath and then BOOM back into the next drop or the next build to the BIG moment. Each time you release that tension, you’re creating a moment where the next time you build that tension back, it’s going to feel more intense and make the subsequent release that much more enjoyable.

As you build and release and get positive feedback in the form of reciprocal flirting, you can take the flirting in different directions; you can be silly or sexy or both. You can do mini role-plays where the two of you collaboratively build on a scenario involving the two of you – why you would just constantly be butting heads on X project because of all the simmering sexual tension, for example. You can play games of what-if or create mini-conspiracies that frame the two of you as a team against the world. You can speculate on who else is on a date and agree that yours is clearly going better. It can be as wild, wide and varied as the two of you care to go.

Similarly, don’t forget that touch is a part of flirting too – and something that starts light and builds. Offering your arm when you’re walking can be gentlemanly or silly, but it’s a way of making it permissible for touch to occur, in a way that’s rarely too forward or unacceptable. A high-five or playful hip or shoulder check at the end of a particularly awesome story, fake palm-reading… these also create opportunities for mutual and reciprocal touch, while also giving folks the room to not touch if that’s what they prefer. And just as with banter or verbal flirting, as things build and you get positive feedback, you can escalate the kinds of touch you do. Continuing to hold someone’s hand after you do a palm-read or as you walk to the next place, a whisper-light touch of the index finger on the inside of the wrist to illustrate a point… these all allow the flirtation and contact to build without being gross or intrusive.

And, just as with verbal flirting, if you aren’t getting positive feedback or they tense up or don’t seem comfortable with physical contact, then you know that they’re not feeling it and you should dial it back.

And one more rule of thumb: if you’re worried about going too far or escalating things too quickly, allow her response to set the limit. If she meets you at the same level of flirting, then that’s where you keep it. If she responds positively, but to a lesser degree, then you dial it down to her level. If she takes the flirting and builds on it or raises… well, now you know that you can raise your end too. This not only helps you gauge her interest, but it also lets her set things to her comfort levels; it’s all too easy to snatch defeat from the jaws of victory or turn someone off because you pushed too hard, too fast. If it’s not mutual or it’s not fun for everyone, it’s not flirting.

Trust me: been there, done that, it ain’t great at all.

However, the most important thing to keep in mind: you need to give yourself permission to do this. Yes, it can be scary at first. Yes, you may feel awkward or ungainly. That’s fine; flirting isn’t about being smooth or suave, it’s about fun. You can be a stammery, shy mess and still be flirting – adorkable is absolutely a thing. But it needs to be something you do together, and something you both enjoy.

So, recognize that dates mean she is already at least a little interested in you. Set the tone from the jump and dip in and out of flirtation as the circumstances warrant, and focus on the build/release method of building tension. It takes practice and a willingness to take risks… but it also means that you don’t have to worry about sending the “I really just want to be friends” vibe by mistake.

Good luck.