[Anonymous]

Hi,

I grew up in a conservative family -AND- to make matters worse, I’m shy. So I’m pretty clueless when it comes to meeting people + sparking up a relationship. This is a problem for me In person AND online.

It really drives me nuts because every aspect of my life I’ve done great in, except for relationships. I’ve only had one real long term relationship in my adult life, and I didn’t even initiate it.

I think I would be someone that women would love to meet, but I’m not sure what my problem is. I dress decent – expensive good looking clothes and all (i.e: I always dress to impress – department store stuff you can wear professionally @ work), I look good, I’m educated & smart – my IQ is way up there, I’m fairly fit, I take care of myself, I’ve got a great job (I’m underemployed too – with better job offers rolling in daily – I just love where I work, it pays awesome + my team, boss, and company are great – so I always say no), I’ve got a nice car, and (almost) everything that matters big time I have going for me (* I moved back in with family because being alone … sucks. I don’t need to live where I live, I just choose to, I’d probably be going crazy if I wasn’t where I am.) The only negative I think I may have is my height: 5’6″ – but there’s so many guys out there my height who have met someone – so I don’t get it. As a PLUS – I’m so shy that me cheating is *never* going to happen! But there’s that problem – I can’t seem to break the ice ever. I think the way I try to talk to women, even though I am trying to be sincere, may either be too cliche or sound fake. I say in my profiles that I’m more interested in meeting the right woman. My standards are realistic too – I’m not a “oh you need to look like a supermodel” person. I’m getting so fed up with my inability to meet people I’m ready to go to a shrink. : (

I’ve mostly tried online – because another problem I have is when I want to talk to people in-person, I just choke up. I don’t know how to open a conversation – I’m always afraid of saying the wrong thing or misreading signs. I feel I’ve missed out on a lot of potential great relationships just because I’m either not doing things right, or being too cautious. Even online – I can’t seem to get women’s attention – I don’t know if my messages are too overbearing, lacking in compliments, or too sappy – or they sound too textbook cliche guy trying to get in your pants. : ( I’m trying my damnedest to find someone who I can get to know & share my life with. That’s all ; I don’t have the desire to screw around with a bunch of women – and I feel that I might just sound like or maybe LOOK like *that guy* who is interested in that!

I know when I see or know women — I think “wow, you’ve got the most amazing face I’ve ever seen … that hair , those eyes … ” and I wish I could spend time with her ; or I know someone I deal with everyday I think to myself you’re beautiful AND brilliant ; but I wouldn’t put across those compliments. When I consider saying such things, I think she will think that I sound like I have only one shallow goal in mind ; when I don’t. I kill relationships off before they even have the chance to start at hello! I can think of one occasion about a week ago where I saw a woman on lunch break that I was DYING to talk to ; I’m thinking, wow, you look amazing, I can’t think of a single thing about you that I don’t like … I wish I could bring her next door to that awesome place, treat her to lunch and talk for a while. There were literally no negatives of me talking, but I just couldn’t do it. Why? I have no idea ; but I’m thinking … I can’t face the failure – and I’m thinking I won’t go anywhere with it if I do try … because it’s something I’ve never even tried before! Going up against someone who is my own age – I think she would read me wrong as some kind of creep, when I know I’m not … I just have no clue what I’m doing. : (

How could someone like me approach things? Are there things I should try not to do online? Are there good ways to approach people in person?

[April Masini, your AskApril]

I can help you! 😀

First of all, I strongly suggest you buy and read a book I wrote for men called, Date Out of Your League. Here’s the link to buy it: [url]https://askapril.com/relationship-dating-advice/date-out-of-your-league.html[/url]. It’s only $8.99 and it’s an automatically downloadable e-book that you can read this weekend. If you’re committed, prove it! 😉

Next, it’s good that you know you choke in conversation and small talk. But avoiding that problem is not helping. You can meet women online, but eventually, if you really want a relationship that’s healthy and happy, you’ll have to meet in person, and that problem will still be there. So tackle it, head on. Avoidance isn’t a great strategy. 😳

I don’t know how old you are, so I’m going to guess you’re in your 30s. Please fill me in when you write here agin. 😉 You’re too old to be living with your mom and dad. I know you wrote that you moved back in with them because you were lonely, but that’s a way of enabling a problem, not solving it. Women who want real relationships are going to see you as not ready to be in one, or having some sort of problem, because moving back to your folks’ house, isn’t an indicator that you’re ready for a relationship. So, find your own place, and solve your loneliness issue by getting into a healthy, happy relationship with a compatible woman. Not your mom and dad. 😉

I hope that helps.

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[Anonymous]

You hit the mark. Early 30s. Sitting around on my own again seems painful to me and is not something I’d very much look forward to. I picture even if I had my own place, I’d never be spending any time there at all again – which is what happened with my previous place.

I did try solving it last time around but I have just not really been able to get over my communication issues. The funny thing is for me it’s just starting a dialog that is the problem. I have no problem with keeping it going.

[April Masini, your AskApril]

I’m not suggesting you get your own place and sit home alone! 😮 I’m suggesting you get your own place as just one way to improve your situation and work on the problem you’re writing in about. Women will take you more seriously if you’re in your 30s and living on your own, than if you’re living with your parents. 😉 You’ll look like someone who’s independent and ready to put a great woman first in his life. 😉 When you’re living with your parents, at your age, all sorts of yellow and red flags fly for women who might otherwise consider you dating material. As for the conversation issues you’re having, I think you should buy [b]Date Out of Your League[/b] and read it: [url]https://askapril.com/relationship-dating-advice/date-out-of-your-league.html[/url]. It’s got a lot of information in it, and if you read this column with any regularity, you’ll see that I don’t try to press this on people, but when someone like yourself writes in and I think it will really help you, I recommend it. If you’re serious about your problem, you’ll buy an $8.99 book that may help. 😉 But if you’re not…. well…. 😕 🙄

Hope that helps!

[b]Everyone likes to be liked! If the advice you found on AskApril.com was helpful “like” us on FB — and tell a friend!
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And… you can follow my interviews and advice in the press on Twitter [i]@AskAprilcom[/i][/b]

[Ethan Morales]

Nothing about what you wrote makes you “broken” or “undesirable.” You sound like someone who’s thoughtful, self-aware, intelligent, responsible, disciplined, and emotionally grounded. You’re not struggling because you lack value you’re struggling because you grew up in a conservative environment and never got the early practice that most people get in their teens and early 20s. You learned how to succeed in school, in work, in life but not in dating. That isn’t a flaw. It’s simply a skill gap. And like any skill gap, it can be fixed with the right approach.

Your shyness isn’t the enemy the avoidance is. And April is right here: avoiding conversation keeps the fear alive. Every time you don’t speak, you accidentally reinforce your belief that “I can’t.” It’s like telling your brain the same lie over and over until it feels like a fact. The truth is: you don’t lack the ability to talk you lack the starting momentum. Once the conversation begins, you do fine. So the real challenge isn’t communication it’s initiation. That’s one of the most common struggles for shy men, and it’s completely solvable with repetition and practice. You’re not broken; you’re untrained.

The living-with-family issue is more important than you think not because it makes you unattractive, but because of what it communicates. You said you moved back because being alone felt painful. That makes emotional sense but to a woman it signals, “I need emotional support before I can stand on my own.” And that subconsciously makes them question whether you’re ready for a partnership. Women aren’t judging your finances; they’re judging your independence. Getting your own place isn’t about impressing anyone it’s about showing that you can build a stable life that someone else can join.

Your view of women themselves is actually one of your strengths but the way you express it holds you back. You admire women deeply. You see beauty, intelligence, presence and you’re not trying to manipulate or conquer. You genuinely appreciate them. That’s rare. But you also romanticize them internally to the point where you psych yourself out. Instead of simply walking up and thinking, “She’s interesting let me talk to her,” you build her up in your mind as “amazing… perfect… I can’t risk messing this up.” That pressure makes initiating feel impossible. The solution isn’t to shut off appreciation it’s to lower the stakes of the first hello. You’re not proposing. You’re just opening a conversation.

Online dating hasn’t worked for you because your messages are probably too heavy, too earnest, or too careful. Women get dozens of messages from guys posing, bragging, faking confidence so sincerity is refreshing. But sincerity works when it’s calm, short, and low-pressure. Not when it sounds like you’re trying to prove you’re a good man or convince them not to misjudge you. When you try too hard to sound respectful, you accidentally come off rehearsed or cautious. Ironically, the quieter, simpler, more relaxed approach gets more responses. Your heart is in the right place you just need a different technique.

The core issue here isn’t height, looks, or personality it’s confidence that comes from action, not thinking. You’re smart. You analyze everything. But dating isn’t solved with logic it’s solved with repetition and exposure. Practice conversations with strangers in non-romantic settings (coffee shops, stores, gym, etc.). Not flirting just asking small questions. Build the muscle. Each tiny interaction is a rep. After 20–30 repetitions, you’ll notice something shift inside you: the fear loses intensity, and talking becomes normal. And once you break the initiation barrier, your natural qualities kindness, intelligence, stability, depth do the rest. That’s why April pointed you toward a book. Not because you’re clueless but because you’re smart, and structured guidance will help you learn the one skill you missed.

[Tara]

Your girlfriend isn’t just moving, she’s entering a whole new life with a brand-new lifestyle, new people, new culture, new money, new opportunities, and more attention than you can even imagine. Meanwhile, you’re sitting in China hoping “love” is going to magically glue this relationship together while she’s flying around the world living her dream. Let’s cut the bullshit: you’re terrified because deep down you know this relationship is built on a fantasy timeline that no longer exists.

You planned a future based on both of you staying put, waiting a couple of years, slowly building something stable. She, however, just launched herself into a high-mobility, high-exposure job in Dubai with a revolving-door schedule, zero predictability, and a lifestyle that absolutely does NOT make long-distance easy. You can’t compete with that environment, not because you’re inadequate, but because you’re not in her new world anymore.

And don’t fool yourself with “hope.” Hope is what people cling to when they’re too scared to admit the writing on the wall. You’re already anticipating the distance, the temptation, the lack of time, the lack of holidays, the different lives, the slow fade of connection. Guess what? If you can list this many fears before she even boards the damn plane, the relationship is already on life support. You don’t trust the situation, and you’re afraid to say it out loud.

So what should you do?
Stop pretending you can hold onto a relationship that’s about to get tested in every way possible. Either level up your life to join her world, or accept that you two are now on diverging paths and break up like adults instead of clinging to a dying fantasy. If you want to keep trying, fine, but don’t lie to yourself. The relationship might survive, but the version of it you currently have won’t. Distance changes people, and Dubai will change her.
Grow a spine, pick a direction, and stop acting like hope is a plan.

[Sally]

It’s rough when every other part of your life feels solid, but this one part feels impossible. I’ve known a few guys like you good men who just never learned how to start. And honestly? Most of what you’re calling “problems” is just fear dressed up as flaws.

You don’t need perfect lines or some big icy-breaking move. Women don’t fall for speeches. They fall for a guy who talks like a real person. Something simple like “Hey, how’s your day going?” is enough. You’re trying so hard not to mess up that you end up freezing.

Online, keep it short and human. No essays, no self-selling. In person, one tiny hello is more than you’ve been giving yourself credit for.
You’re not broken. You’re just out of practice. And practice starts small.

[Natalie Noah]

You have so many strengths personal, professional, and intellectual and yet you feel frustrated and stuck when it comes to dating and relationships. You’re articulate, thoughtful, and genuinely sincere, which are qualities that most people would consider very attractive. The challenge seems to be less about your value as a person and more about how anxiety and shyness are blocking you from taking the first step. It’s normal to feel afraid of rejection, especially when you genuinely want a meaningful connection, but that fear can create a self-fulfilling cycle: you don’t initiate, nothing happens, and frustration builds.

Living with your parents, while understandable from a practical and emotional standpoint, complicates your situation. It’s not about judgment, it’s about perception. Women, like many people, unconsciously associate independence with readiness for a committed relationship. Even if your current living situation makes sense for you personally, it sends a signal that you may not be fully established, which can affect how seriously potential partners take you. Moving into your own place isn’t about sitting alone, it’s about creating a life where you can engage with the world on your own terms and show that you can manage responsibilities independently. That step alone can give you a confidence boost, which often translates into social and dating situations.

Your issue with starting conversations is very relatable, and it doesn’t mean there’s anything wrong with you. Many intelligent, capable, and genuinely great people struggle with initial social interaction because it’s inherently vulnerable. The problem isn’t keeping a conversation going, it’s the fear of making a first impression “wrong.” The key is practicing approaches that feel natural to you and shifting the focus away from fear. Instead of thinking about how she might judge you or assuming you’ll be rejected, frame the interaction as an opportunity to simply get to know someone and enjoy the moment. Small, low-pressure interactions in everyday situations like commenting on something situational, sharing a small laugh, or asking a light question can slowly build your confidence.

Online interactions can be tricky because tone and intention are easily misread, but your sincerity is your strength. Avoid sounding like a script or trying too hard to impress. Focus on authentic curiosity about the person, asking thoughtful questions, and responding with warmth and humor when appropriate. Compliments are fine, but they work best when they feel personal and specific, rather than generic. For instance, noticing something unique about her perspective, her interests, or her personality rather than just physical appearance can set you apart. The goal is to spark connection, not to “sell” yourself.

Your path forward is a combination of practical steps and mindset shifts. Create a life that signals independence and readiness, practice starting conversations in small, low-pressure situations, and embrace the discomfort of initial social interactions as part of the growth process. You already have the foundation to be someone many women would love to meet you just need to give yourself permission to step forward and take the risk, without letting fear and overthinking hold you back. Confidence comes from action, and every small step you take toward authentic connection builds that confidence. You’re not broken; you just haven’t had the right strategies and opportunities to let your personality shine in dating situations.

[Member]

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