Approaching Someone You Like

No one likes rejection. Let me emphasize that, NOBODY likes to be rejected! So, it’s hard for both men and women to find the courage to approach someone they’re attracted to. Everyone has an experience where they were in some type of social venue, like a coffee shop, and they caught eyes with someone they were attracted to. In a split second, you make the decision, “Should I look away or not…”. Sometimes how a person responds to you when you first meet matters a lot, and sometimes it doesn’t. Everyone has times where they get nervous and have trouble communicating their real feelings.

I’m currently single, so I see a few women I want to talk to when I go out and about. Well, honestly I rarely run into single women who I’m attracted to. Which could mean that my standards are too high, or maybe I’m getting old, or I need to get out of my environment and socialize with other single women I’ve never met before. I think it’s a little bit of all three ☺.

You can’t do the same thing over and over, and expect different results. If you want change, you have to change.

Yesterday, I did my usual Sunday routine–went to church, I did some shopping, and I went to the coffee shop to do some work. I really didn’t plan on seeing or talking to any attractive women; but during the day there were a few women that caught my attention.

At church, I saw an attractive woman sitting in front of me. She was probably either in her mid-to-late twenties or early thirties. I could tell she was trying to be cute; she wore a stylish hat during the church service (it was cute). Even though I have a rule of not approaching women at church, because (generally speaking) church people are messy and fake (and I love my church!). But, like anything else there are exceptions to every rule. I just would want her to get to know me without other people (who think they know me) getting into our relationship. So, anyway, I chose not to approach her. I wasn’t so afraid of her rejecting me, I just didn’t feel like it. Plus, I know the opportunity will always be there.

After church, I went to Whole Foods for lunch. As I was picking different toppings for my salad, I noticed an attractive woman next to me doing the same thing. She was wearing her afternoon t-shirt and shorts, so I know she’s not really trying to impress anyone. She was also with two young kids, probably around the age of 5-8 years old; but, who knows if they were hers or not. It doesn’t really matter. I also noticed she wasn’t wearing a ring, so I’m thinking to myself, “Should I go and approach this woman?” After purchasing my items, I saw her sitting outside with the two kids, and I chose not to approach her. Honestly, I did something that I regret. I stereotyped her without speaking to her. Whether if I was right or wrong, she just looked like someone who would be hard to connect with on different levels.

Yesterday I was tired. I probably drove over 12 hours Friday and Saturday combined, so I was traveling all weekend. So, Sunday I just didn’t have enough energy to deal with approaching anyone. Some days are better than others.

So, when I do have the energy, how do I go about approaching a woman I’m interested in? Well, it depends. It’s always easier to engage in conversation with someone if you’re in a common environment, like work. Or, if both of you are alone somewhere, like a coffee shop. I usually will approach her, look in her eyes and introduce myself.

“Hey! How are you? My name’s Jason…. listen to how she responds, because everything you say after that depends on her response. I feel most women already have a close idea of what a man wants when they are approached, they just want to see how they go about getting it.

I for one love talking to attractive women, flirting, and feeling the romance that comes with dating. It makes me happy to smile and engage in good conversation. Even though we all have been rejected when approaching someone you liked… I feel in many cases being rejected has little to do with who you are, but it matters more who you approach, when/where you approach them, and how you do it.

For me, when I approach a woman, it’s because I’m attracted to her and my intent is to get to know her better. I’m trying to get her attention. A few days ago, someone I knew messaged me a naked pic of herself trying to get my attention. Well, it did get my attention. I blocked her. That’s not the way I want to be approached by a woman. Regardless of anything else, I feel approaching someone is all about three things:

  1. What they want… and what you want.
  2. The atmosphere you’re in.
  3. Your confidence level.
svg7 min read

Jason Perry

I'm a black man with Christian values. A father to my son, a friend to those who desire my friendship, a lover of life and even more...

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This is my journal, my journey, and my perspective in life – JP

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