Approaching women – Ultimate guide with 25 flirting examples
Mental Health

Approaching women – Ultimate guide with 25 flirting examples

Very few men can approach and get to know women in a friendly and confident way. The fear of rejection is deeply rooted in a man’s psyche, and in reality, you won’t get anywhere with hackneyed pick-up lines – in fact, the opposite is usually the case! A typical pick-up line comes across as clumsy and cheap

to most women, and this immediately ruins any chance of a flirt or interest on their part. To help you overcome your fear of approaching women and being rejected, this article provides you with the ultimate guide with every conceivable technique for skillfully approaching a woman, as well as 25 tried and tested ways to start a conversation with a woman in a friendly way in any situation.

8 basic tips for confidently and correctly approaching/getting to know women

First of all, it is important to look at the basics of how you can open a conversation in a fear-free and confident manner.

The most important rule when approaching women:

If you want to approach women, your appearance and self-confidence are far more important than any flirty or pick-up lines! Therefore, below you’ll find a total of 8 extremely important tips that are guaranteed to significantly enhance your flirting/the first few seconds of conversation:

1. Establish eye contact with the chosen one

  • A confident look shows her that you have self-confidence and you can also clearly see her interest in you through longer eye contact
  • Never break your eye contact downwards , this symbolizes insecurity and submissiveness
  • Eye contact when flirting is critical, but don’t stare at her creepily like Count Dracula

2. Look for common ground before approaching and consider a second sentence

  • Often the conversation stutters after the first oh-so-great saying, so think not only about the icebreaker, but also what you say afterward
  • Her small tattoo on her arm, for example, can be just as good a conversation piece as her eye-catching, creative necklace

3. Don’t hesitate! The 3-second rule is critical

  • as soon as you start thinking about it, you will lose (guaranteed!)
  • Count “1 – 2 – 3” in your head , breathe deeply and then walk over, because when you count, other areas of the brain are activated and the fear of approaching someone decreases significantly (it really works – try it!)
  • take a deep breath (point 5) and then go over immediately

4. There is no perfect pick-up line

  • slimy pick-up lines are almost always embarrassing for both parties
  • A casual “Hi, I know it’s a bit unusual, but I just noticed you and I wanted to spontaneously come over and say hi!” is almost always enough
  • Below you will find numerous tried and tested examples of how to approach your dream woman

5. Smile is the language that is immediately understood worldwide

  • Through the mirror neurons in her brain, she is encouraged to smile back and positive feelings are automatically triggered in her
  • especially at first eye contact (see point 1), a friendly smile can be perfectly combined to break the ice
  • Make sure you have a friendly facial expression, not only when flirting from a distance but also when you go over and talk to the woman

6. Nervousness is absolutely OK – you can talk about it

  • Shyness and fear of approaching are absolutely normal, especially in the beginning
  • You can also bring it up with something like: “I have to honestly admit that I never do this kind of thing, so I’m a little nervous… but I just had to stop by and get to know you!”
  • Many women will like this honest and sensitive way
  • This slight thrill is what makes flirting so exciting

7. Get to the point

  • Women love men who are self-confident , know what they want and communicate it clearly
  • Even if you initially ask indirectly for directions to the bus station, you must show your clear interest after 1 – 2 minutes at the latest
  • Before you end the conversation, you can signal clear interest by exchanging contact information, with something like: “Hmm, that’s been a really pleasant conversation. You seem interesting to me. I have to move on now, but let’s stay in touch on Instagram / exchange numbers.”

8. The result doesn’t matter

  • How many men do you know who can approach any woman in any situation? Exactly! Probably almost no one. Therefore, no matter how your flirtation turns out: Unlike others, you’re a go-getter who has the courage to go out there !
  • Approaching women and learning how to flirt properly is a learning process and with a little practice your shyness and fear of approaching will definitely decrease

Ok, so how exactly does “ approaching women â€ť work ?

You don’t have to be particularly creative to break the ice. You can approach a woman in any situation, for example by paying her a little compliment about her dress or her hair. Everyone loves compliments , and this indirect approach means she can’t react with rejection.

Or if you’re particularly shy and afraid of being rejected, you can just ask her a simple question . This is also an indirect way of getting to know women, according to the motto: it doesn’t hurt to ask. No normal person will take offense if you ask for the time or directions .

Such approaches don’t come across as pushy at all and can confidently initiate a flirtation. Don’t make it more complicated than necessary, and again: stay away from any slimy pick-up lines ! It’s embarrassing for everyone involved!

25 examples for approaching women & flirting better in every situation

Below you’ll find tried-and-tested flirting tips on how to approach women and how you can finally get your fear of approaching them under control . Just look at each of the following 25 flirting examples and consider whether it suits you or your personality . If one or more of these suggestions appeal to you, feel free to add them to your flirting repertoire and confidently approach a woman with them the next time you get the chance. Good luck!

Once you’ve overcome your shyness and fear of approaching women, you’ll find plenty of interesting topics of conversation here to get to know each other and have an exciting conversation .

1. Approach women – “ask for directions”

“Hi, excuse me, but can you recommend a bar/restaurant/shisha bar/cocktail bar nearby?” â€“ That’s super simple. Just giving a quick description will break the ice in just a few seconds.

After that, you can move on to other topics of conversation. Sure, you might be telling a little white lie if you’re actually from the area , but honestly, you can then package that as a lighthearted joke and use it to your advantage. Something like: â€śTo be honest, I have something to confess! I’m actually from out of town, but I just had no idea how else to approach you!” Definitely

a friendly way to approach a woman and better than any fake pick-up line!

2. Meet women – “interesting tattoo”

For example, if she has a tattoo, an interesting pendant, or other unusual jewelry: “Hi, quick question. Tell me, does this tattoo with the flower of life/yin-yang symbolism look really interesting? Does it have a deeper meaning for you?” Just show genuine interest, and she’s guaranteed to make time for a quick chat. After all, that’s exactly why she got a tattoo: to stand out!

3. Approaching women – “Could you please take a photo?”

If you’re out in a group and see an attractive woman, you can ask her to take a group photo of you and your friends . Almost everyone will be happy to do this. You can then thank her sincerely and start a conversation at the same time. It’s a lot of fun, super easy, and requires almost no effort.

4. Appeal to women – “Fitness bracelet”

Fitness trackers are widespread these days, and you can easily start a conversation about them. You can use various aspects to approach the topic.

For example, you can pretend that you’ve recently been thinking about getting one yourself and then ask, with interest, about the possibilities for optimizing sleep, monitoring your heart rate, improving your calorie balance , etc. In almost all cases, she will be interested in such a discussion, and you can then easily transition to topics like exercise, nutrition, and health in general.

5. Approaching women – “Are you just as cool?”

“Hi, excuse me, but I just had to come over and find out if you’re as cool as you look?!” – That’s funny, and at the same time you’re targeting her inner values , which works particularly well with physically very attractive people!

This is so helpful because this line has a qualifying and, of course, slightly manipulative effect . At this point, she obviously doesn’t want to react inappropriately, because that would give herself a negative character assessment. Nobody wants to do that voluntarily!

After you’ve opened the conversation, you can of course continue with any other obvious topics of conversation .

6. Approaching women – “Bon appĂ©tit!”

For example, if you’re eating at a cafeteria and you catch eye contact, you can politely say “Bon appĂ©tit!” as you pass, accompanied by a friendly smile, of course.

This is especially useful if you’re a bit shy. This initial encounter breaks the ice, and the next time you see her, it’ll be much easier to start a conversation or maybe even sit down right away .

7. Approaching women – “Gym”

In public, you constantly encounter women carrying a gym bag. You can, of course, use the gym bag as an indicator that they’re visiting a gym . At this point, you could start a conversation with, for example, “Hi, looks like you’re on your way to the gym.” She’ll almost certainly say yes.

Now you can elegantly enter the conversation with a little flirtatious lie/white lie , telling her that you ‘re currently looking for a new gym and asking her about the price, the sauna area, the free weights area, the classes on offer, etc. Viola! And you’re in the game.

8. Approaching women – “Do you have a light?”

“Hi, do you have a light?” – If you actually smoke, this conversation starter is an absolute classic , not just in public , but also in front of bars or clubs . Nobody is stingy with a bit of light and if so, then you should definitely stay away from that person! After this simple question, you can immediately move on to topics like “I just can’t kick this stupid habit!” / “Favorite cigarette brands” / “What made you start smoking in the first place?” / “Have you ever tried to quit smoking?” etc. You can also use this conversation starter if you are not a smoker at all. Simply borrow the party stuff, light it up a bit and when she asks what you are doing? – answer with: “To be honest, I had no idea how to talk to you and the only thing that came to mind was the lighter! ” Then she’ll almost certainly start laughing, and you can (only if you want!) relight the lighter, let it burn, and add something like, “I can simulate a candle here for us both, so we can get to know each other. Romantic atmosphere and all that, you know…” If done correctly, this is a real hit, but it requires charm and a lot of self-confidence.\

9. Approaching women – “Macbook”

Let’s assume she’s sitting there with a MacBook, looking at the screen and typing something. You could easily go over and ask: “Hi, tell me, do you also have the problem that your MacBook charging cable keeps breaking at this predetermined breaking point? I’ve had four of them break!”

Most Apple users, and I myself, have repeatedly responded with: “Absolutely, that ‘s a real disgrace, considering the prices. That never happened to me with my previous Windows computers!” That’s another example on this list of how you just need to look a little more closely and can use pretty much anything to start a conversation .

10. Approaching women – “Hey, high-five!”

This is particularly good for getting to know women in clubs. If you’re in a good mood, you can simply make eye contact as you walk past , hold your hand in the air, grin, radiate extreme positivity and ask for a handshake with a verbal “high five!” .

This works particularly well in bars and clubs . If she reacts just as positively to you, you can also hold her hand, stop her and immediately respond with “Hey, you’re cool!” or introduce yourself by name “Haha, by the way, I’m the…” This is a relaxed and funny way not only to break the ice, but also to make initial physical contact at the same time (extremely important!).

11. Meet women – “in the university library”

In the past, when I went to one of the university libraries to study, I would look for a seat near a woman who seemed interesting or likeable to me. Then, when I needed to go to the bathroom, I would close up my laptop, walk over a few steps, put it on her desk and ask her to look after it for two minutes. No decent person would say “no!” at this point, right?

After a few minutes, I would come back, thank her and take my laptop with me. Every now and then, when I got my laptop, I would point at the laptop, pretend it was a pet and make a little joke like “I hope it hasn’t done anything wrong and has been good!” â€“ that would always put a smile on the lady’s face and lead to a short conversation.

From that point on, the ice was broken and whenever I ran into her later on campus, in a lecture or in the cafeteria, I could start a conversation with a simple “Hi” . Most of the time, however, I started with small talk in a whisper right there in the library .

It’s a conversation starter that requires virtually no effort, as it’s just a simple question: “Excuse me, can you look after my laptop for two minutes?” . Again, who would say no to that? Everyone knows you shouldn’t leave your things lying around unattended. Plus, you’re showing her trust , which is really important!

You’ll notice that these approaches are shockingly simple and pave the way for a conversation in small steps . They’re perfect for effortlessly using your surroundings, a specific situation, or a simple request as a conversation starter with a woman.

12. Approaching women – “nice boots / nice shoes”

The following conversation starter is extremely effective, but you need to be incredibly self-confident and maintain solid eye contact. If you see a woman wearing nice shoes or boots, you could start the conversation something like this: “Hi, excuse my direct manner, but I need to come over here and say something: I noticed your boots!” – That’s it, at this point you don’t say anything, but maintain friendly eye contact.

She would then normally react with some surprise and logically ask what exactly you meant by that: “You noticed my boots? What do you mean, do you like them?” – at this point you could, for example, exaggerate in a funny way and say something like “Ohhh yessss, I looooove them! Especially the heels! Where did you get them? I want to get the exact same ones!” . Again, the note: This way of approaching women is more for advanced flirting .

13. Approaching women – “at the gym”

Sporting activities offer another perfect everyday situation for flirting. If, for example, you see her doing yoga poses, push-ups, or other exercises in the gym or on the fitness trail, you can bring that up and comment with a hint of admiration .

Here’s an absolute classic conversation starter in the gym: “Cool, those are really really clean push-ups. And especially so many!” – or if she’s doing the splits – “Wow, pretty impressive, I could do that when I was 14! All my ligaments would probably tear now.” – she would then comment with something like, “I danced ballet as a little girl and have never neglected the stretching exercises since then…” – here you have the keywords ballet and childhood, which you can of course pick up on straight away and easily expand the conversation on the reasons for ballet, other hobbies, or childhood memories .

14. Meet women – “Hat with a bobble”

Just like in the example above, you can draw on other things you notice and spontaneously use them to start a conversation. For example, “Hi, I noticed your hat, the huge pompom is really cute! I had one just like that as a child…” This

is a very simple and honest way to open with a compliment. And remember: people love compliments! But only give one compliment during an interaction, otherwise it will come across as suck-up and you’ll just shoot yourself in the foot!

Here, too, you shouldn’t get hung up on the conversation starter itself and overthink it! Remember: the conversation starter should only start the conversation, no matter what you use for that (a tattoo, a hat, boots, or a sports bag). How confidently you deliver it is much more important when approaching women!

15. Meet women – “Further training / open-plan offices / lectures”

People in your immediate circle, for example, who work in the same open-plan office, attend the same university courses, or are currently doing a training course with you, can simply approach you in the cafeteria with, “Hi, I don’t know you at all. I’m (insert name here). We’re attending the same economics lecture, I think…”

From there, you can then bring up more obvious topics, like the cafeteria food or the topics of the training course . This is truly one of the easiest ways to get to know a woman.

16. Approaching women – “Can you please keep this brief?”

For example, if you need to get your wallet out, take off your jacket, or tie your shoelaces, you can simply ask her to hold your shopping bag, jacket, etc. for a moment . This approach is especially helpful in situations where you’re both standing still, such as waiting in line or at a bus stop .

17. Meeting women – “Is this place still free?”

You can ask if the seat next to her is still free at university, on the subway, on the train, or on the bus . This is a particularly easy icebreaker, as it’s unlikely anyone will think of denying you the seat. However, you must then initiate the conversation immediately, for example, with a statement like, “It’s so cold today!” If she’s interested, she’ll jump in.

18. Approaching women – “Queue at the supermarket”

If you’re standing directly behind or in front of her in the queue at the supermarket, you can sigh briefly and make a comment like “This is taking FOREVER, they could open another checkout!” – If there is basic interest on her part, she will start the conversation with a short counter comment and you’re in the game.

19. Approaching women – “Cute dog!”

If she’s walking a dog or playing with it, just ask as you pass: “That’s a cool dog! I’ve always wanted one. What breed is it?” From

here you can then go further and be interested in the life of a dog owner ( how time-consuming is it, how loud is the dog in the apartment, can it do tricks, etc. ).

At this point, pretty much every woman will want to present her dog in the best possible light and proudly show off its tricks . From here it shouldn’t be a problem to steer the small talk towards other topics.

20. Approaching women – “Cheers!”

If you’re walking through a bar or club with a drink , simply look her in the eye as you pass, say “Cheers!” and raise your glass .

If you feel a liking for her, then it’s best to take the opportunity to start a conversation straight away , or go for another round later and the next time you meet her you can say a simple “Hi” because at this point the ice has already been broken and you’re no longer such strangers.

21. Getting to know women – “asking about their origins”

In many cases it is possible to ask a woman about her origins. You can simply pretend that she reminds you of someone. If you also speak English or another language that is appropriate in the case, you can open with that.

Here’s an example: “Excuse me, do you speak English?” – at this point most people will say yes “Yes, a little bit.” – “OK great, just a quick and free compliment for you: You look absolutely gorgeous!” – every woman will understand that and feel flattered by the compliment. This breaks the ice.

Later or immediately after, you can also ask if she speaks German too. In the vast majority of cases, she will of course say yes, and you can ease the situation by saying something like: “Ahhh, ok, great! You gave me a very Latin American impression. I have a friend who looks exactly like you, and that’s why I thought you might also be from Colombia. Well, that’s why I spoke to you in English. It could have been…” – from here you can then continue with further questions, assumptions, or statements that you can observe in order to develop the conversation.

This conversation starter also leads to a very strong frame at the beginning, because women often get a little nervous in such cases when they suddenly have to assert themselves in a foreign language. However, because you then switch back to German after 20 seconds, she relaxes massively and is suddenly fully present (this effect has a much greater impact on the interaction than you might think!). From this point on, you can have a relaxed conversation for a few minutes.

Of course, speaking to her in a foreign language is only one option. You can just as legitimately go over and ask her directly if she is from this or that country because she looks extremely similar to a very good friend of yours and she has foreign roots.

22. Approaching women – “I have no idea…”

“Hi. I honestly have no idea how to address you, but I’ll just do it.” Delivered with the right smile , this is a truly charming way to break the ice.

If you’re feeling unsure about starting the conversation, you can calmly address this fact and say, “Hey, I’m honestly a little nervous right now, but I just wanted to stop by and say hi.” The nice side effect of this is that addressing your nervousness usually dissolves it automatically after a few seconds.

23. Getting to know women – “Do we know each other?”

Just ask: â€śHey, is it possible that you used to go to that… kindergarten? / school? You remind me so much of someone I used to play with in the sandbox.” â€“ that’s a bit of a white lie , but childhood memories are associated with a lot of emotions (from here you can move on to topics like favorite toys, memorable childhood moments, first childhood friends, etc. ).

24. Approaching women – “Read a book”

An absolute classic: If she’s reading a book, at first glance it might seem like you shouldn’t disturb her, but honestly, that’s just an excuse! Someone reading a book isn’t putting out a fire, and if you ask a friendly and interested question like: “It’s rare to see people reading books! Everyone else just stares at their smartphones like zombies! That book must be really exciting. What exactly are you reading?” â€“ she’ll almost certainly find this indirect compliment funny and join the conversation in a friendly manner.

25. Approaching women – “while swimming at the lake”

In the same way, I have approached girls dozens of times while they are sunbathing by the lake with another effortless question. For example, if she is sitting alone, sunbathing and looking at the water, all I have to do is walk over, sit down and, without making eye contact , while looking at the lake, simply ask “Hmmm, you’re probably thinking about going in, but you’re worried that the water might be shockingly cold?” – immediately after asking this question, I turn towards her, smile at her and she automatically joins in the conversation.

It’s so simple, you could almost say unimaginative! But it works ! And if I get bored of the conversation, I can always get up, thank her for the conversation and step into the water.

Important: Use every opportunity in your daily life to overcome your fear of approaching people and your shyness forever!

All the options described above will never be a substitute for hard practice, no matter how effective they may be. Because, again: The content of the initial conversation is absolutely secondary; the way you approach the other person is far more important!

How can I approach women who are currently busy?

If you would like to approach a target person but they are obviously focused on something else, you can use this observation to open the conversation , e.g.: ” Hey, I see that you are… in a hurry / eating / reading a magazine …, but I just had to come over and get this off my chest: … ” At this point you continue and then build on the conversation with appropriate topics. Even

if many people think it is inappropriate to approach someone in such cases because they are obviously busy at the moment, you can defuse the tension by describing the current situation. What’s more, this introduction will then take around 10 seconds longer, which means you can score points with appropriately positive body language and tone .

What should you do if the woman becomes slightly distant or seems very surprised when you approach her?

In such a case, correct (social) calibration is particularly important. If, for example, she looks at you slightly puzzled after you have approached her, simply reply briefly with a relaxed smile: ” Hey, don’t worry, I don’t want to rob you and I don’t want to sell you anything! I just wanted to come over and say hi… “.

If, on the other hand, she or he seems reserved and unfriendly right from the start of the conversation, you can easily and humorously soften the feeling with something like: ” Man! You’re ruining this entire Disney-like fairytale romance that’s been hanging in the air between us! I’m afraid that’s about it. I hope you have a wonderful day anyway! “

This way you can very politely get out of the situation or salvage the whole thing by making her laugh after all . Please also remember never to approach women from behind , put your hand on their shoulder, or start the conversation while following them from behind. This immediately appears anything but attractive and self-confident to almost all women.

Additional tip: Strengthen your self-confidence with visualization exercises

It also makes sense to take 10 minutes a day to mentally rehearse your favorite conversation starters. This is a particularly effective technique if you are currently a bit shy and want to learn to come across as more likeable (using the Benjamin Franklin effect) .

Lie down for 5 minutes, relax a little, and then visualize the situation as best you can . Go through it in your mind’s eye: walking up to her, opening the conversation, her smiling at you, and joining in the conversation. This type of practice will not only help you gradually lose your fear of approaching her , but will also help the various possibilities sink into your subconscious.

This way, a possible conversation starter will easily spring to mind when a similar situation arises. This way, you won’t let this opportunity slip through your fingers because you can’t think of anything better than some unsuitable excuse.

In addition, you should replay the conversation starters you actually experienced that didn’t go particularly well in your mind and mentally smooth out the things that could have gone better. This is an approach from neurolinguistic programming and is particularly helpful for cognitively correcting suboptimal experiences.

Hello! My name is Scarlett Walton — I’m a former practicing psychologist and now a writer dedicated to helping people find emotional balance, inner peace, and personal growth. For over 12 years, I worked in the field of psychology, supporting individuals through anxiety, relationship challenges, and major life transitions. My Professional Journey I began my career in a private therapy practice in Chicago, where I counseled adults and teens on self-esteem, anxiety disorders, and emotional healing. Over the years, I conducted more than 5,000 sessions, took part in educational programs, and led workshops of my own. But at some point, I realized I wanted to share my knowledge with a wider audience. That’s how this blog was born. A Personal Story A few years ago, I went through a painful divorce. It was a turning point in my life. I experienced the full spectrum of emotions I had helped others navigate for years. That was when I began to write. I felt a strong desire to reach out to those going through difficult times — even if we couldn't meet in person. Writing became more than self-expression for me. It became a continuation of my therapeutic work — through words, advice, personal stories, and emotional support from afar. The Mission of This Blog This blog is a safe space for anyone seeking answers, encouragement, or simply a bit of inspiration. I share not only professional insights but also real-life experiences, reflections, and practical advice rooted in years of practice. I truly believe that words can heal. If even one of my articles helps you feel a little more understood or a little less alone — then I know I’m on the right path. Welcome, stay awhile, and most importantly — be kind to yourself 💛