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How to Know if He/She Really Likes You/too shy and anxious, how can i have more confidence talking to men I like?


I am sure I am much older than nearly all of the people who ask you questions, but oh well. I am in my thirties, have never been married, have no children. I have dated very, very little and have had just one sexual relationship that was fairly brief. I have never been in love, which is also painful in addition to what I will also say. I have suffered from major anxiety all of my life regarding talking and approaching men I am interested in. The anxiety has improved with medication, but I still have an extremely hard time starting conversations with men I like and almost always do not flirt much at all. I very much prefer the man to make the first move. If someone shows interest without any doubt, then I can flirt back, but until I am totally sure someone is interested, I am just so afraid of rejection and looking like an idiot if I am wrong about their signals. I work in a very small store with a small group of employees. Another employee I like, and he just gave me a couple of signs that may indicate he's interested, but I can't tell if he is just being friendly or flirting. First of all, we have not talked too much in depth since he is a pharmacist and is pretty busy much of his shift. I work in another area. Anyway, a couple days ago, I was walking past the pharmacy and he said hi, waved, and gave me a big smile. A couple hours later, he was going out to buy milkshakes for the remainder of us who were still working. When he came up to me to ask me if I wanted one, he didn't look me in the eye and was acting nervous. I have a feeling he may be shy with women, but don't know this for a fact. Was he showing interest when he smiled and when he got nervous when he asked me if I wanted the shake? He was kinda stumbling over his words a little bit. I want to ask him out because I just want to get it over with already and start going out with him, dating. Is he just being friendly or what?  If he is interested, is it too early to ask him out? We have talked before, but the conversations have been really brief because it's usually when he is buying something and people are waiting behind him in line. He always seems happy to see me and always greets me and smiles. Should I hold off a bit on asking him out if he is interested? Is he even interested at all? Or would it be awkward and/or too early to ask him out? As I said, he is usually pretty busy at work so there are not a ton of chances and time to talk to him for more than two-three minutes. I probably would have to catch him when he is leaving, I suppose. By that time I am usually not too busy with customers. One more thing: I thought he was a little older than he is- he is 26 and I am quite a bit older. I'm not sure if he knows this or not , but obviously he could find out my age because I have some prescriptions. I have a feeling he thinks I'm younger though, closer to his age. And I am afraid if he knew I'm a decade older than him, he would freak out. So that bothers me. But I don't have an issue with dating a younger man since he seems very mature. Your thoughts and advice is greatly appreciated!!  Thank you!

Hi Holley,

My apologies for taking so long to get this back to you. Let's get right to your question, yes?

From what you've shared with me in your letter, it does sound to me that he's interested in you, at least on a basic level. So, I don't think there would be any harm in trying to talk him a bit more, and yes, even flirting with him a little bit. One thing that can help you with flirting is that the point of it all it to have fun, and make both people feel good. In other words, don't take it so seriously. Keep it light and playful. For example, if you were to tell this guy that you were looking for a job, and he asked you what kind of job, you might say something fun like, ''Oh, I wouldn't dream of telling you, then you'd only want me for my money.''  Or when you pass by him, you might ask ,'' And how is my biggest fan today?'' while smiling at him. See, being playful and flirty like this does two things: one, it helps you to boost your own confidence, which will make you a bit more bold throughout this situation, and two, in both of the examples I mentioned, you're doing something quite awesome - you're assuming attraction. When you assume attraction on his part while talking to him, it lets him know that you're hot and you know it, and it becomes something of a self-fulfilling prophecy.

As for asking him out, I think that you most certainly should. Where I think you can start, and to give yourself a better gauge of just how interested he is in you, I would suggest you invite him out for a group date a couple of times first. Invite a couple of your coworkers to go out with you and do something fun, and of course, invite this guy along, too. It'll give you a chance to see what he would be like as a date before you actually have an individual date with him, and it will also give you some more confidence to even get to that point, because since other  people will be there, too, there won't be any pressure on you.   I know that this sounds scary, but I know that you can do it, Holley. I have every ounce of faith in the world in you. :)

I hope that this helps, Holley, and if you have any more questions, I'd be happy to answer them.



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Everyone gets confused sometimes when it comes to matters of the heart. We all want to know if that special someone at school or work was winking at you, or if if they just had something in their eye. I can help you find whether your intended likes you, signs to look for if you're unsure, and can help you in the right direction on where to go from there. I will be timely, personable, and friendly with you; it'll be like talking to an old friend. Give me a try; I bet I can help you! *Update* Because of rising expenses, I must say that I can only accept questions with a $2 donation. With the lengthy, friendly, and in-depth response you'll get from me, it will be well worth it. Thank you for understanding.

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