[Unsporty]

Hi,

I have had a lot of bad experiences when approaching women. From your regular I’m-Not-Interested, to outright disdain. I know it’s part of the “job”, so to speak. The thing is, nowadays, whenever I feel any kind of attraction, whether physical, personality-related, or otherwise, towards a woman, I immediately back away. To give you an example, whenever an attractive woman comes into the office where I work, I turn to the computer screen, and barely say a word. Instead letting my colleagues do all the talking. I see it as a combination of lacking faith in my abilities to flirt “properly” (I’m 40, and I only have one success story in my life, and only because I had someone guiding me through the process), and the fear, not only of the woman’s reaction, but also that of the onlookers. Even if I think a woman is demonstrating the slightest bit of interest, I tend not to act on it, because I am afraid of seeing things that are not there, and thereby making the proverbial fool of myself. You could say it is as if I am constantly looking for the mother of all green lights. I know I have a long way to go, but I think the first step is learning how to flirt confidently. How do I begin to climb back this hill? Thanks.

[Ask April Masini]

You’re afraid of failure and rejection. Which is normal — but also something you need to overcome so you can enjoy romantic relationships and not miss opportunities. Basically, you have to do a couple of things. First of all, get out of your head. You’re not the only person to be rejected — we’ve ALL been rejected. In fact, think about baseball. The best players, the ones who hit it out of the park, strike out most of the time. But when they do hit it out of the park, it’s glorious! So know that you will fail — but you won’t fail all of the time, and that everyone else is doing the same thing.

Next, you have to find a way to be okay if you’re uncomfortable. Rejection is uncomfortable, but….. it’s a real shame to lose out on opportunities with women, simply because you’re avoiding possible discomfort. Nobody died of rejection, and you have to learn to pick yourself up and move on if you are rejected. So understand that rejection is part of a good life, and accept it.

Third, practice makes perfect. Flirting is an art, just like conversation is. Practice it and get better at it. If you don’t practice it, you probably won’t get better at it. So take every opportunity you can find — the coffee shop, the gas station, the elevator, parties, movie theatre lines — and flirt. Simply start by smiling, then add in compliments. and finally questions and conversation.

Let me know if this helps and write me back and tell me how things are going.

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[Unsporty]

Hi. Thanks for your reply. I will see what I can do and come back here from time to time. I don’t really go out much these days, but I will try and find some way to at least practice. Even if it is just talking to people at work. I should have added that one of the reasons why I don’t talk to women at the same time as other men, is because I both think I can’t “compete”, and because I am afraid that my attempts will be noticed by the men as well. Also, I find it hard to try, because there is noone there to tell me what it is that I did wrong, in case I fail. Case in point. I recently took a post-graduation, and I was very much attracted to a girl in my course. But at the same time, it was as if I avoided being alone with her, because I never felt confident that I could make a conversation flow, or was afraid that she would notice something. Furthermore, when I went to a dinner at a mutual girl friend’s house, and I heard her say some guy from the course was “gorgeous”, it just discouraged me from trying anything. I am very easily discouraged, as you can probably tell. And when we all went home to work on our final dissertation, even though she had said we might discuss sources, bibliography, and that sort of thing, I never got in touch with her, because I was afraid she would reply to, say, a Facebook message, in real time, and I would be unable to sustain a conversation. I chose this example, because it’s the more recent one. So, I have a long way to claw back. But I hope I can share some doubts and questions regarding future events. Once again, thanks.

[Ask April Masini]

You’re letting your fears run your life. 🙁 It’s GREAT that you’ve identified them, but now you have to conquer them. If you don’t, you’re going to live with regret, which is probably one of the worst situations ever. Re-read what I wrote about nobody dies from rejection. Everybody takes a pie in the face some of the time, and until you’re ready and willing to risk rejection, you won’t get a big prize, ever.

If you need to “talk” more about this, here, just write back. I hope you’ll get out there and practice flirting — it’s going to help you enormously. And I know it’s a big deal for you but I do think you can do it and do it successfully. Let me know how it goes.

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[Unsporty]

Hi. I thought I’d come back and give an update on how it has been so far. Obviously, there isn’t an immense amount of progress. And I know it wouldn’t be expectable to be so. As I live a bit far from town centre, and don’t have a car, it becomes hard and more expensive to go there in my free time. Also, being a bit of a scaredy cat, I don’t wanna end up in the wrong part of town (I moved here not long ago). Maybe in the future I will explore more and find out more about the nightlife of this town. I have had plenty of bad experiences with girls in bars and clubs. Not just simple rejection, but actual fake interest and subsequently being laughed at in the end. But anyway, I digress.

For the time being, my only chance of flirting and making conversation is at work. I have noticed a couple of different girls. One looks a bit bashful, and I had the chance to talk to her a bit near the coffee machine. It becomes harder when she comes into my office and another guy is talking to her. I feel that, if I am going to try, it has to at least make some kind of sense to engage in conversation. If I just barge into the conversation of others, it might look too forced or uncalled for. So, for now, I count on crossing paths in different areas. Another is objectively very attractive, but her attractiveness has sort of diminished in my eyes due to her appearing to be a combination of flirty and smiley when she needs something, and aloof the rest of the time. There are a couple more, but I haven’t really crossed paths with them. I have managed to make conversation with others, so I may use that as practice for the future. Of course, I say this not knowing if the company even has a policy on these things. Based on the Christmas party description, it doesn’t. But, if nothing else, maybe it can help me for other occasions.

Tricky stuff, but I want to go on. Trying to figure out upcoming steps.

[Ask April Masini]

Unless you live in a city where public transportation is the norm, like Manhattan, why don’t you buy a car? If you can’t afford one, why not get a better job — or a second job, so you can? Having a car is important for dating in cities where you have to drive to have a social life. 😉

As for your bad experiences in bars, with women, you didn’t die from any of them! If someone rejects you — and even laughs at you — they weren’t right for you anyway, so don’t let those bad experiences get you down. Dating is a numbers game, and you have to keep trying in order to increase your odds. 🙂 Also, don’t forget that clubs and nighttime social venues are only a small fraction of the places you can meet women. Parks, coffee shops, volunteering and even food shopping are all great places to meet women! 😀 Keep working on meeting women and flirting with them. You will get better with practice. 😀

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[Unsporty]

Hi again.

Well, I think I have realized what my biggest problem is.

It’s my mind going totally empty, when I am in the presence of potential flirting targets. Either that, or it fills up with just random words, random phrases. Things that I feel would, instead of making me sound pleasant, make me sound like a weirdo. And I don’t just want to shout out the first thing that pops into my mind. Is this overthinking? Am I too afraid of being conspicuous?

Anyway, what can I do to combat this issue? Can/Should I practice at home? Is there any reading material I can use?

Thanks.

[Ask April Masini]

Nope — you can’t practice flirting at home. 😉 You’re 40 years old — you have to get out there and practice in real life. 🙂 Just say hello. Then follow up with a compliment or a question. If you’re at a coffee shop, simply ask her if she’s tried the pumpkin lattes — or whether she lives around here. If you’re at a dinner party, start the conversation with, “Hi, I’m so and so.” It’s that easy. 🙂

You can ask a woman about her work. About something you see in front of you like her dog, her car, the book she’s reading…. You just have to do it. And the more you do, the more practice you’ll accrue and the better you’ll get at it.

Don’t get phased by rejection. It’s normal and it’s part of the game, but do keep going and don’t stop. In the course of a single day, you should try flirting with 20 different women — whether it’s the dry cleaner, the postal worker, the bank teller, the woman behind you at the bus stop or the coffee shop — wherever you are, there’s opportunity. 😀

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[Ethan Morales]

Your experience is completely normal many men reach a point where past rejection, embarrassment, or ridicule creates a fear loop that stops them from even trying. You’re overthinking, self-conscious, and hyper-aware of how others perceive you. The truth is, your fear of failure is controlling your behavior, not your genuine attraction or personality. Recognizing this is the first step, and you’ve already done that which is huge.

The main problem isn’t women, it’s your mindset. You’ve internalized bad experiences and let them define your interactions. What April points out that rejection is a part of life is key. No one gets it right every time. In fact, the men and women who succeed socially are often the ones who have “failed” a lot, learned, and kept going. You’ve got to accept that a little embarrassment or rejection is temporary, not a reflection of your worth.

Confidence comes from action, not preparation at home or in your head. You cannot practice flirting in isolation. You need real-world interactions brief, low-stakes moments to build a comfort level. This could be at work, in a grocery line, coffee shop, or any place you can make casual conversation. Smile. Compliment something observable. Ask a simple question. Keep it light. You’re not trying to seal a lifetime commitment in a single chat; you’re just learning to navigate human connection naturally.

Start with micro-actions. Say “hello” to women you encounter. Compliment or comment on something neutral like their book, coffee, or jacket. Then move up slowly: ask a question or engage in a two-minute conversation. These little successes build confidence and prove to your mind that rejection isn’t catastrophic. The more you do it, the more your fear will fade.

Avoid comparing yourself to other men or worrying about “onlookers.” That’s irrelevant. The only person who matters in the interaction is you and the woman you’re engaging. When you treat conversation like practice and connection rather than a performance, it becomes less scary and more natural. Remember: this is a numbers game. The more women you talk to, the higher your chances of a meaningful connection.

Logistics help too. April mentioned transportation if getting out is difficult, consider ways to increase your social mobility. Even small steps, like local cafés or community events, give you consistent practice and exposure. Your biggest barrier is mental, not physical. Focus on building comfort with small interactions, and your confidence, ability to flirt, and social ease will grow naturally.

[Sally]

When you have had enough bad reactions, your body learns to duck before anything even happens. That does not mean you are broken, it just means you have been embarrassed enough times that your brain thinks it is protecting you.

But flirting is not some magic trick other men have. It is just small, human signals. And you do not have to jump straight into asking someone out. You can start with the tiniest things that do not risk much at all.

Say “hey, how is it going?”
Hold eye contact for a second longer than feels comfortable.
Smile when you greet someone.
Make one light comment about something real, not a line, not a move. Something simple like “rough morning?” or “that looks like a good book.”
That is it. That is flirting. It is not cleverness, it is warmth.

Start small. Start where you are. You do not need the mother of all green lights. You just need a moment where you let yourself be seen, even a little. And the confidence comes after, not before.

[Author]

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