How To Flirt Without Being Creepy: 5 Pitfalls To Avoid

It’s almost a lose-lose. Come on too strong and freak her out; don’t come on strong enough and get overlooked. So let’s set the record straight - what are 5 no-go creepy dating behaviours you need to avoid, so you can flirt without being creepy? 

For over 15 years I’ve worked as a dating coach to men and women so I’m one of the only dating coaches in the world who gets to hear both sides of the story. This means the advice I’m going to give you today on how to flirt without being creepy, isn’t just talking from my own experiences, it’s also how thousands of my female clients view dating! 

Note: I also won’t be sharing tips that are glaringly obvious (“don’t stare at her boobs!”) instead I’ll be focusing on the subtle codes of social conduct that you may accidentally break, in the process of getting to know her. 

How to flirt without being creepy: 5 pitfalls to avoid

1. Too much, too soon 

In dating it’s often difficult to get the balance right of how much interest to show in her. Many times, I’ve seen great guys accidentally creep out the women they’re dating by coming on too strong. 

Particularly in a time when people are meeting on dating apps, and there’s so much negative messaging (“love bombing, anyone?”) on social media about dating; women are cautious. They’ve often had more than one experience of choosing the “wrong” guy and don’t want to make that mistake again.

Women are also very sensitive when they perceive a man to be more interested in them, than the other way around. If she senses you’re much more interested in her, this is a time when flirting can easily come off as creepy. She will feel she hasn’t contributed enough to the relationship to deserve that level of interest, or that your interest is founded on putting her on a pedestal, not engaging with who she actually is. 

Part of this also simply comes down to how men and women are different. Men often approach dating with a mindset of “she’s my type great - how do I impress her?”, whilst women are typically slower to develop attraction, and more discerning. This creates an environment where it’s easy for her to misread your attempts to impress her as you are coming on too strong. For example:

• You match on an app and you ask her out right away. You’re cutting to the chase, but she feels like that’s inappropriate as you don’t know her at all yet. 
• You’re an affectionate guy and you want to make sure she knows that this is a date. You end up overusing the heart emoji, or kisses, and she gets turned off.
• You’re excited by her and are chatting away to her non stop, to make sure you don’t lose her interest, and ironically this behaviour does just that. 
• You’re sending her pictures of your day, and giving lots of details about your life, but she’s not reciprocating. (More on this later.) 
• Perhaps you’re getting carried away with the idea of dating her and you’re quickly suggesting that you come over and help her with something, or telling her that she’d get on well with your sister. 

What could be happening here is that you are a warm, open guy looking to connect. However, by getting the tempo of this interaction wrong you will overwhelm her with affection before she’s come to any decisions about you. She could quickly see your attempts to flirt as needy, or worse assume you’re love bombing her, and run a mile.

How to flirt without being creepy top tip: Your job here is to learn to cool it off until you get to know her better. Try to approach dating with a similar mindset to her, i.e. ‘she seems great so far, but what other qualities would I really need to see in her before I’d consider her as a romantic partner?’ 

2. The connection isn't mutual

For a woman to feel attracted to you she needs to feel like you’re able to take her feedback on board and read the room as to how she’s feeling. Knowing when to stop pressing forwards is a key way you can flirt without being creepy. If you keep plodding forward (whether that’s with a topic of conversation, or asking her out) without noticing that she’s given you a clear signal to “stop” or isn’t participating in your suggestions, you will come across like you’re woefully unattuned to her signals. Or worse, creepy. 

I get it. You’re checking out to see whether persistence pays. You think she might be attracted to a guy who is ‘calling the shots’. Or perhaps you’re repeating an anecdote because you can’t understand why she doesn’t get that your story about paragliding is seriously cool. 

Here are some straightforward examples of how you could get this wrong: 

• You really like her, and she did seem quite interested at the beginning, so you keep asking her out in a variety of ways. You suggest all kinds of different dates. All she does in return is dodge the question, or say she’s a bit busy right now. If you keep trying to logically solve the problem (for example making a note in your diary for when she’s less busy!) you’re avoiding the hard truth, that she’s just not that interested! Keeping knocking on the same door, without a clear yes, is an easy way for you to appear like you have no options. 
• A more subtle way you could communicate the same message is when you don’t notice when she’s showing no enthusiasm for a topic of conversation, a date idea or even a sexy comment. Even if you think your idea sounds great, or you read on a dating coach’s blog that all women are driven wild when you tell them so and so; if she’s not appearing engaged or trying to further the conversation, drop it. Pushing your point will make you appear like you have low levels of social awareness, because she’s clearly not participating with you, and you’re continuing to not take feedback.

How to flirt without being creepy top tip: Have a clear rule of thumb for yourself when dating that you need reciprocation or you’re dropping it. Sometimes the most powerful verbal skill you can learn to help with this is acknowledgement. Simply saying, “I like you but just so you know this is the last time I’m asking,” or “okay that story bombed, damn, I thought that was so funny,” allows you to notice her, and take command of the conversation, even if it’s not 100% going your way. This level of awareness is sexy, pushing on without taking feedback is creepy. 

3. Agenda is too regimented

Being too attached to an expectation of how you’d like things to go, can blind you to how things are going in the present. Again, this will wind up in a cycle of you pushing your plan, without the level of interest from her to justify it, and wham you’re back being creepy. Here are some examples of how this could happen:

• You’re convinced tonight is the night and are excited to take your relationship to the next level. Maybe things go so far and she expresses that she’s not sure. Here some pick up advice of old would probably tell you to keep pushing, and that ‘she doesn’t really mean it’ when she says ‘no’ or that she’s ‘not sure.’ Or that if she’s at your house she “knows” she wants to sleep with you. Ouch. That advice has not aged well. Please don’t ever do this. On the better end of the spectrum you could have bad sex that she then regrets, and so stops speaking to you. On the worst end of the spectrum she could easily view this as you not having gained adequate consent. All of this can be avoided by having a standard for yourself that before you have sex with her, you need enthusiastic consent. If that’s not there, saying, “hey, don’t worry I have a master’s degree in patience” or “if you’re not into, then it won’t be fun let’s just relax and do something else,” will smooth this over. Often seeing you be totally unattached to the outcome of sex is one of the most attractive things you can show as a man. 
• The same could be true of any moment you create an expectation that your relationship is at a certain level without verbally communicating this to her first. Don’t assume she’s your girlfriend before you’ve had “the talk” about commitment. If nothing else it can be incredibly awkward to happily talk to people about your “relationship” when she then informs you she thought you were just casually dating. Dating can be tough when you realise that the person you’re interested in isn’t on exactly the same page as you. However you can flirt (and move your relationship forward) without being creepy by simply stating how you see things. 

How to flirt without being creepy top tip: Get into the habit of telling her how you see things for example, “I like you and at this stage I’m not really interested in other matches on dating apps” is a good way to spearhead the “what are we” conversation. Likewise you could also say, “look I’m attracted to you, but I have zero issues waiting, I want us to both be on the same page.” By checking in with her you’ll get clear verbal feedback as to where you are in relation to her. Without this you’re just guessing, and could come off as creepy if your assumptions are wide of the mark. 

4. Being too explicit

If a man says, “you’ve got great tits,” this is generally received much more positively from a boyfriend, and far less positively from a random guy in the street. Whilst this is (thankfully) not something that many modern men would even consider doing, there’s a lesson here on how to flirt without being creepy. 

That is that 99% of the time women will not receive explicit comments on their body or appearance well from men they don’t know. 

• That doesn’t have to be the stereotype of a guy on a construction site, it could also quite easily be a guy on a first dating app telling her that she’s got beautiful eyes. Again from a man she knows she’s attracted to, this will be flattering. From a man she’s not sure she’s attracted to this could cause her to cringe “oh man he really likes me, what the hell can I say back to that??”) 
• This is also why women will recoil if you compliment her in a way that’s too explicit before her mind is really in that gear. For example if you kiss at the end of a date and you say, “I’m looking forward to doing that again!” Whilst she’s not yet sure if she wants to do that again it will be a huge turn off. 

How to flirt without being creepy top tip: Whilst you might think it’s hot to talk about her body or to do some cheesy innuendo, this isn’t erotic for her at all. A good rule of thumb is, don’t talk about how you’d like to touch her body, until you’ve actually consensually touched her body. 

5. Disregarding social norms 

Women love socially intelligent men. For women, showing that you understand the subtle, and explicit, rules that govern our society is also very important to how attracted they feel towards you. Show a masterful level of social etiquette, impress her friends with your wise cracks, and have a great retort for every time she’s on the fence about you, and she’ll fall in love. Do something that’s socially “odd” and she may at worse perceive you as dangerous and unpredictable. Here are some examples of how you could get this wrong:

• Overtly hitting on women who are way too young for you. Whilst yes some women do like older men, and if you’re Leonardo Di Caprio no one cares; for the majority of men a very large age gap is likely to chuck you into the “creepy old man” camp. 
• Overtly hitting on women in socially inappropriate places, like the workplace. Recently big companies like BP have even made it a contractual obligation to declare relationships in the workplace. The “Mad Men” days of workplace affairs are well and truly behind us. Of course relationships between co-workers still may happen, but I would actively avoid seeking them out.
• Hitting on women using physical compliments in a place where they feel attention is already being drawn to their body, for example the gym. Tell a woman that she’s got a great physique at the gym or the spa and she may feel even more vulnerable than usual. Again, it’s not that it’s impossible to talk to women at the gym but you’ll want to kickstart the conversation on more neutral territory. Crack a joke about how hard the instructor is pushing you today, and introduce yourself, don’t tell her how good her leggings look on her. 
• Trying to kiss a female friend when she had no idea that you were romantically interested in her. 
• Sitting too close to someone on public transport. If there’s plenty of seats available don’t sit next to the attractive woman, give her some space. If you catch her eye, smile, gesture and if she signals she’s open to talking, ask if you can sit with her for 2 minutes. (Then stick to your word and get up and move off when you say you will.)  
• Approaching a woman who is walking alone at night. Again this is a sure fire way of making a woman feel incredibly frightened. Don’t go there. 

Remember, context is everything. Be very cautious when you read dating advice online (even mine!) that it may not apply to your exact personal situation or circumstances. To avoid being creepy you need to look carefully at the social context: How well does she know me? Is this a place where she could expect a man to approach her in a romantic way? If it’s not socially “normal” to approach her how can I use what I say to her to mitigate this? If I want to talk to her, how can I do just that and not linger? If I’m unsure can we swap eye contact and see if she smiles back at me first? 

How to flirt without being creepy: 10 quick tips 

1. Don’t linger in her personal space without saying anything to her.
2. If she indicates (verbally or non verbally) that she’s uncomfortable, immediately drop it.
3. Do comment on who she is, not how she looks. (Saying that she’s got great energy or you like her confidence will work much better than talking about her looks!) 
4. Do keep any physical compliments general, “you look nice today” rather than specific, “you’ve got great legs”. 
5. Don’t touch women who you don’t know.
6. If you’re on a date, start with a brief touch to her arm to see if she’s comfortable with this level of contact. 
7. Do ask for consent before you make a physical move on her (eg. kissing her). 
8. Don’t comment on her looks at all if you’ve met through the workplace. 
9. Don’t stare. Look at her for 1-2 seconds maximum to see if she holds your eye contact. 
10. Don’t send her explicit messages or images. 

How to flirt without being creepy at work 

1. Avoid hitting on colleagues. 
2. If you feel like you’ve organically formed a connection with a woman at work, approach this interaction with a lot of caution. 
3. Start by suggesting you grab a coffee or lunch 1-1. If she’s at all open to getting to know you better she’ll be open to this.
4. Over your coffee break, suggest you’d like to talk more, ask if she’d prefer for you to communicate on office channels (slack, email) or would it be better to take her number. 
5. For a first date suggest a more neutral daytime setting (lunch, coffee etc). 
6. If she asks you about your intentions, say that you like her, but your work life is really important to you, so you’d rather be sure about your connection before taking this any further. 
7. Continue to spend time together but draw a line on physical contact until you can both have a conversation to establish that you’re on the same page.
8. If you begin a relationship, discuss how you might handle things at work if your relationship doesn’t work out. 
9. If she decides she no longer wishes to date you, accept her decision and don’t seek out further contact than is necessary at work. 
10. Be polite, cordial and professional towards her even if she doesn't share the same feelings as you. 

How to flirt without being creepy over text

1. Don’t keep messaging her if she’s stopped responding.
2. Don’t look for excuses to keep contacting her if she’s said she wants space. 
3. Don’t message her on another channel (i.e. social media) if she’s stopped responding to your messages. 
4. Don’t ever turn up uninvited to try and talk to her if she’s stopped replying to your messages. 
5. Don’t use romantic emojis (hearts, kisses etc) unless this has been initiated by her. 
6. Don’t send her explicit images if she hasn’t explicitly requested these. 
7. Don’t message her non-stop.
8. Don’t become angry if she takes longer to respond than you do.
9. Don’t consider yourself to be in a relationship with her until this has been developed in the real world. 
10. Don’t do a deep dive into her social media and comment on something she did 2 years ago. 

My intention in writing this blog isn’t for you to feel more restricted, as I really understand how hard it can be as a man to make a romantic connection; and I also know you may already feel a degree of shame around communicating interest in women. However, I do want to coach you to be able to engage with women in a way that’s nuanced and socially aware. Hopefully this blog has given you some ideas for how to flirt without being creepy!