You are here:

General Dating Questions/should I ask him out or wait a bit longer?


Hi. I am in my thirties and have always been very shy when it comes to making the first approach with a man I like. It's just difficult for me to make the first move, especially if I'm not sure he's into me or not. Since I'm very shy at first, I am not comfortable flirting either and again, this applies to if I'm not positive there is an attraction toward me. I like this man I work with and have a feeling he MAY feel the same way, but don't know. He's always been friendly to me, so maybe that's all it is. Yesterday he was working in his area (we work in different areas of the store)and he saw me several feet away and greeted with a big smile and wave. A little while later, he came up to me and was right next to me. He was buying shakes for everyone and when he asked if I wanted one, he couldn't look me in the eye and seemed nervous. Yes, I know you don't read minds, but was he flirting with the smile? Did his nervousness indicate he is maybe shy but is interested?  I am clueless sometimes about reading flirting signals because I can't tell if it's flirting or just being friendly.  I want to just ask him out already, and I know I can be bold enough to do it, but should I wait it out a little first? Since I don't really even know if he's interested? But I get the feeling that he may be. Honestly, I'd rather just get it over with already and ask him because I just wanna start dating him already!! What do you think? And was he flirting or just being friendly?

Hello Holley!

Welcome to the experience that 99% of men have to face too - being afraid of the initial approach and not knowing if the other person is attracted. The good news is that you're actually willing to do it - I'm VERY proud of you! Yay Holley!

The reality is; I can't tell you what he thinks of you from just being nervous and offering you a shake. The MORE important reality is this: it doesn't matter anyway!

Holley, think about this: if you approach him and invite him to have a drink, what's the big deal? You would actually invite him to spend some time with a great girl who thinks he's the shit. Are you really telling me that he would reject you? I sincerely doubt it!

Of course you don't have to bite off a huge chunk here. Just make it simple. You can just say, "You know, we've worked together for a while and I don't really know much about you. We should grab a drink one day after work. I'm around on Thursday or Friday - which is better for you?"

Is that really that scary? It's not a big deal at all! Being attracted to someone isn't a psychological disorder - of which there are plenty of others. You're just connecting with another human being; and let's face it, if things go well, HE'S going to get something incredible out of it! Don't make this bigger than it really is - yet.

Be bold! The mighty forces will come to your aid. They always do.

Best regards...

Dr. Dennis W. Neder
CEO/Executive Producer
BAM! Productions
Remington Publications
Producers: "BAM! TV" and “Love and Sex”
Publishers: "Being a Man in a Woman's World I, II & III”

General Dating Questions

All Answers

Answers by Expert:

Ask Experts


Dr. Dennis W. Neder


I'm able to answer any sort of question related to the approach, meeting people, dating, sex, relationships, break-ups, non-legal marriage and divorce questions, and anything in between. I've helped over 30,000 people with their individual issues. IMPORTANT: Please, PLEASE don't ask me, "what was he thinking..." or "why did he say..." types of questions! I DO NOT READ MINDS! There are 1,001 reasons why someone does what they do, says what they say or thinks what they think. If you *REALLY* want to know what they were thinking, saying or why they were acting that way - go ask them! Be sure to check out my FAQ's on my website at: You can email me directly at:


I am the author of the books "Being a Man in a Woman`s World I & II" and "1001 Places and Techniques to Meet Great Women" and 11 others. I`ve spent the last 20 years studying the art and science of every aspect of relationships, and have answered over 30,000 letters from readers all over the world. My main focus is men`s relationships with women, but I also have many female readers and answer questions for them regularly as well.

Doctor of Philosophy

©2016 All rights reserved.