The Courage to Say Hello: A Shy Guy’s Guide to Approaching Love

He said hello, and I responded with a smile. He was a fine-looking young man, and we were both at the National Service Secretariat district office to submit our appointment letters for endorsement. He said, “Wow, you actually responded! Back on campus, I swear I never would’ve had the courage to say hi… From afar, you seemed so unapproachable and out of my league.” He smiled, repeating “wow” over and over. I felt moved by his confidence, so without hesitation, I offered my contact information.

Before we even left the building, my phone chimed — it was him, sending me a half-page introduction. I was a little taken aback; in my head, I thought, “We literally just spoke…” But clearly, he was overjoyed. Later, he messaged again, saying, “Today, I got my favorite meal to celebrate the courage to talk to my crush. Please, can we be friends?”

That night, as I reflected on my day, I wondered, what must it feel like for guys to approach women they find attractive? For some, it’s natural. For others, it’s like studying a six-credit-hour course, or worse, like enduring six years just to finally say, “I like you, and I want more.” If they were studying medicine, they’d have graduated by then!

Does it come down to a lack of confidence, or is it just the fear of rejection? Many guys worry they’ll ruin a good friendship for something uncertain. Others may just like to take things slow… but six years? That’s a bit much. For me, six months to a year is enough time to make up your mind!

Curious, I asked some male friends about the most “out-there” or “unconventional” things they’d done to get a woman’s attention or win over a crush.

One friend said: “I don’t usually do weird things to get a lady’s attention; I just act naturally. But I did end up paying for her waist beads when we met. She didn’t have enough money and was haggling for a lower price. I heard her, so I stepped in and covered the difference. We chatted for a few minutes, then exchanged contacts.”

Another friend confessed: “I went so far as to join her interdenominational choir! I couldn’t sing, but I learned just to get closer to her. I never missed a rehearsal, and eventually, we got to know each other. We’re not together now, but it was fun while it lasted.”

One even braved an allergy: “I ate food I was allergic to! I saw her at this cozy restaurant, so I asked her for a recommendation. She suggested what she was eating, so I ordered the same thing and tried to look brave. We exchanged numbers, but as soon as her perfume wore off, I realized she had a strong body odor… I was out after that.”

There’s the Sunday Ironman: “Every Sunday afternoon, after church, I’d go to her hostel to iron her clothes for the week. She’d cook while I ironed and would pack me a take-out. But trust me, I don’t even like ironing! It worked for a while, but eventually, we just stayed friends.”

And then, the “Best Friend”: “I was her friend, the one she told all her dating stories to, even details of her first time with a guy. I never asked to be in the bestie zone! I tried to guide her on safe practices, even buying her emergency contraception once. But every time she got comfortable enough to change in front of me or rest her head on my shoulder, I felt hopeful… only to have my heart broken when she said, ‘You’ll always be my bestie.’ To this day, I don’t like hearing that word.”

Finally, the Classic Wingman: He said, “I took what seemed like an easy yet frustrating path—befriending one of her friends to get closer to her. I’d constantly check in with her friend, asking how she was, if my name had come up in their conversations, and whether she was interested in anyone or dating anyone. Thankfully, her friend assured me she was single, so I thought it would be smooth sailing from there.

But I was wrong. I was still a student and tight on cash, yet I ended up sacrificing most of my lunch money to treat her and her friends. Not just once, not twice, but over and over again. Honestly, it felt endless! Eventually, though, the effort started to pay off. I played the role of ‘lover boy’ as best I could, and after a few months, we finally clicked. We officially became a couple.

Ladies, it’s time to rethink the “hard to get” mindset. That guy you’ve been eyeing might be struggling to gather the courage to approach you, or dealing with his own insecurities. Don’t be afraid to make your interest known. No, I’m not saying to throw yourself at him; a simple, honest conversation can go a long way.

And to the guys: We understand you better now. We promise to be more considerate, even if it’s a no. But we’d love to see you show some confidence, too. Forget the childhood conditioning or past rejections — you deserve a shot at love, just like anyone else.

For those who’ve been single for years, not by choice, but because of fear or a lack of confidence, here are a few practical steps: to help shy or less confident men regain confidence and approach women with ease:

1. Work on Self-Confidence

Build self-esteem: Take time to appreciate your strengths and interests. Regularly engaging in activities you’re passionate about will naturally increase your self-confidence.

Set personal goals: Aim for small, achievable goals like improving a skill, working out, or learning something new. These milestones reinforce self-worth and boost confidence over time.

2. Develop Positive Self-Talk

Replace self-doubt: When negative thoughts like “She’s out of my league” pop up, counter them with affirmations like “I am good enough, and I have something to offer.”

Practice visualization: Imagine yourself approaching a woman with ease, having a friendly conversation, and leaving on a positive note. This mental practice can help ease nerves.

3. Practice Social Skills Gradually

Start small: Approach new people in general situations—start conversations with baristas, co-workers, or people at events. The more you practice friendly interactions, the easier it’ll be when approaching someone you’re interested in.

Engage in group activities: Joining clubs, classes, or hobby groups will give you chances to meet new people naturally without the pressure of one-on-one situations.

4. Learn Body Language Basics

Be approachable: Maintain open, relaxed body language—avoid crossing your arms or looking at the ground.

Practice eye contact: Making eye contact shows confidence. Start small by holding eye contact for a few seconds in regular conversations before trying it in romantic settings.

5. Approach with Friendliness, Not Pressure

Start casual: Begin the conversation with a simple greeting or observation about your shared environment, like, “Hi, I’m (Your Name). This place is really great, isn’t it?” This is low-pressure and doesn’t immediately signal romantic intent, allowing the conversation to flow naturally.

Focus on getting to know her: Ask genuine questions that show interest in who she is, like “What do you enjoy doing in your free time?” This approach shifts the focus from impressing her to learning about her, easing nerves and creating a relaxed environment.

6. Don’t Fear Rejection

Reframe rejection: Remember, rejection isn’t a reflection of your worth. Sometimes, timing or circumstances simply aren’t right. Keep a lighthearted perspective and acknowledge that not every approach will lead to a connection—and that’s okay.

Practice resilience: Each attempt is a learning experience. The more you try, the less intimidating it becomes, and over time, you’ll naturally build resilience.

7. Be Genuine and Stay True to Yourself

Be yourself: Authenticity is attractive. Rather than trying to act in a way you think she’ll like, let your personality shine through. Confidence comes from feeling comfortable with who you are.

Focus on having fun: Instead of worrying about the outcome, focus on enjoying the conversation and experience. This relaxed energy will make a positive impression.

Remember, confidence is a journey. Each step you take builds momentum, and over time, approaching someone will feel as natural as any other conversation.

At the heart of every approach, every conversation, and every risk lies a simple truth: love is about connection, not perfection. So, to the shy ones, to the silent admirers, and to those who hesitate at the thought of saying hello—remember, each time you reach out, you’re not just daring to meet someone new; you’re daring to embrace your own worth.

True courage isn’t found in the absence of fear, but in facing it head-on. Whether you succeed in love or simply learn along the way, every attempt makes you a little bolder, a little braver, and a lot more alive. So take a deep breath, trust in yourself, and let the world see who you really are—because you deserve the chance to be seen, loved, and valued, just as you are.

With Love,

Rammie.