How to Get Over the Fear of Approaching Women Because You Feel You Will Make Her Uncomfortable

This is a shortened version of a comment from a reader that I feel many men probably can relate with: (You can read the entire comment here as well as my response.)

Reader’s Concern:

I don’t even know her besides her first name and where she works. I don’t even know if she is single or not… It’s not fair to her because she doesn’t even know me at all. How does a guy “just stop in” and try to change the situation without being a creep or causing problems for her at work?

We had a good time talking, and shared laughs. She did say to come back. Is it just wishful thinking? How long to wait? … Maybe I’m over analyzing this and should just forget about it.

Any thoughts?

First Part of My Response:

First, I want you to get out of the mentality that it’s not “fair” for her. When you said, “It’s not fair to her because she doesn’t even know me at all,” you’re not realizing that everyone starts off as a stranger, in that very position, and us ladies are VERY grateful to the men out there who still feel it their responsibility to approach a woman.

It takes the load off of us, and so it’s not a matter of “fairness,” which makes it sound like what you are doing is a bad thing instead of an honorable, good, masculine thing.

If anything, you taking that risk is what is not “fair.”

I just want you to go into that situation believing I’m doing her a favor by making this easy for her instead of It’s not fair she has to be approached by this stranger and be made to feel uncomfortable.

Why? Because if she is interested, she won’t be uncomfortable. She will psyched, excited, happy, elated, and ever so GRATEFUL that you were so bold.

If she is not interested, in that VERY brief moment, she will feel uncomfortable, but so will you. So it is FAIR.

And then you dust yourself off and leave the premises giving yourself a mental congratulations because you did the risky, hard thing. You did something out of your comfort zone. You did something manly. And you are that much closer to feeling more comfortable in that kind of situation just because you have put another solid approach under your belt. You are adding to your experience and therefore your level of comfort.

Best case scenario, she could one day be thinking this about you:

But it won’t happen unless you make it happen. She could never make the move because she works there and THAT would be inappropriate for her, and she could lose her job! That, and a gazillion other reasons why women don’t approach men.

I don’t want to get ahead of ourselves, but I just want to make sure you are going into the situation with the right mindset, the confidence that what you’re doing is a GOOD thing, you are doing HER a favor by taking the risk for both of you.

All great love stories begin with a man who had “wishful thinking” and just went for what he wanted. The sooner you act upon this, the better it will be for your psyche, and so you don’t develop oneitis. You can read about oneitis here.

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I love thinking about the intricacies of dating, love and life. I share my tiny lessons in the hope that it helps you as you navigate the dating world.

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  1. L. T.

    So, I’ve been doing a lot of reading here, and I can definitely see that a few things are very VERY important to you. First and foremost, you are ALL about taking risks and being as aggressive as possible, a try-it-until-it-works kind of thing. The second thing that shows up here a lot is that love is a risk, and that it’s supposed to be an even thing with both parties pulling evenly. But I don’t see much about women taking risks in love. I’m not judging, I’m just pleading ignorant. If it’s supposed to be even and there are things woman are doing out there that are hard and risky, I’d like to know about it. It would make me feel a lot better knowing that I won’t always have to face all of love’s little gambles by myself.

    • MidoriLei


      Oh, thank you for your frankness! You are so right! I talk a lot about love being a risk. Unfortunately, I don’t really tell woman to “take a risk” like I tell the men to. This seems highly, highly unfair, right? Where do I get my reasoning?

      Being a Christian, I get it from the fact that in the bible, a husband is metaphorically linked to being like Christ, while a wife is metaphorically linked to being like the “church,” or the bride of Christ. See, in the Bible, Christ is the one doing all the pursuing of “the church.” The whole reason why “the church,” falls for Christ is because he FIRST loved the church. (1 John 4:19)He is the one doing all the sacrificing (he died for the sins of his bride), and he left the comfort of heaven and paradise to come to this imperfect world to rescue his bride.

      The risk that Jesus took in coming here and trying to woo his bride (the church) is that he could have failed. He could have sinned and not lived a perfect life. Then he wouldn’t have been able to save her.

      But, Jesus has confidence that once he pours his love on his church, He knows that once he has “chosen” his people, they cannot help but fall for him (to accept his sacrifice).

      All of this is Christian imagery so it might be all knew or confusing. But being a Christian writer, this is where I get my beliefs.

      Also, the bible talks about how a wife is valuable to a husband. She is a “helper” for him.(Genesis 2:18) She is more valuable than jewels.(Proverbs 31:10) Just by a man finding a wife, he obtains favor from God. (Proverbs 18:22)

      Do you see that all of this implies that it’s the man’s job to look for this gift? Why should the “gift” look for her recipient? She is the gift, so she is the one that gets pursued.

      And lastly, it is a man’s job to find her:

      Proverbs 18:22
      He who finds a wife finds a good thing and obtains favor from the LORD.

      Nowhere in the bible does it attach this responsibility of the pursuit to the woman or the wife. Although there is the story of Ruth, the widow who practically threw herself on Boaz (she came to him while he was drunk and sleeping on hay), she is the exception, not the rule, and I truly believe that she had to do the “pursuing” in her situation because it was another man’s job to take over for her deceased husband, so Boaz was not entitled to pursue her unless she say something and ask him to step in.

      Where do the women have to take the risk? There is a different kind of risk women take. They take a risk in “helping a man out” by looking approachable, smiling, and making herself the best possible candidate in the waiting process. The risk she takes is in waiting and believing that someone is out there (not fearing she will be alone forever). She just needs to be warm, kind and inviting. She needs to know her role and accept it as the natural order of things instead of throwing herself at men, giving sex up and expecting them to want to commit to her forever. When she doesn’t treat herself like a “jewel,” like a “gift,” then she devalues herself.

      But I don’t tell women they should just play hard to get and tease a man forever. Like I said, she has an active role of being approachable and warm. But, the man, he is the pursuer.

      When a woman pursues a man, she will forever wonder if he really wanted her, or if she just made it convenient for him.

      And when a man gets pursued by a woman, he cannot appreciate her in the same way had she waited for him to do the pursuing. Granted, he can love her and appreciate her, but I honestly, honestly believe that had he done the pursuing, the “working” for something valuable, he would appreciate her to the fullest extent.

      So this God created system of roles benefits both parties. Nowhere in the bible does it say that it is not good for woman to be alone. It was Adam who first felt the pang of loneliness, the longing for a partner. And Eve was created to be his helper and companion. Adam didn’t really take a risk cuz in his mind, he just knew this woman was made for me.!

      And that’s how I feel like it’s going to be for a man who has finally met the partner he was supposed to be with. The risk isn’t going to even feel like a risk because in his heart, he’s going to know they belong together. But that’s just me being sentimental. lol. I know that’s how it was for my husband. I’m sure he was nervous when he first called me, but he pursued me to the altar because he just knew we belonged together.

      I just tell men to take the risk because by the time they meet their match, they will be more comfortable:)

      Does that make sense?

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