Hello there!

I can relate to this! I was an ugly duckling in high school. At 15 I got a complete overhaul and moved to a new place. Overnight, I was popular; and I had hard time navigating the social environment. I’m still awkward and uncomfortable in social situations; even though I’ve spent most of my work life in customer service type jobs.

It really sounds like you have a good head on your shoulders. There’s a lot to be said about someone who has made their own way in the world and has such financial responsibility as you describe. You will make a great partner when you find the right person to share your life with! So, let’s talk about finding yourself, first.

I think that your loneliness and the perception of the “ticking clock” might be creating a sense of urgency that tempts you into settling for someone who doesn’t have your best interest at heart. Now, when I was in the throes of infatuation with the heartbreaker, I am not sure that I’d have been able to take the advice I’m about to share. It’s something that I had to experience for myself; and you may be the same. But I’ll throw it out there, anyway.

It all sounds so cliché, but it really is the truth. You must love yourself more than you love anyone else. You can work on this while pursuing the sociopathic dream woman; but it may take a lot longer. When you truly love who you are and what you represent as a human, then your fear will dissolve.

Examine the fear. Sit quietly and imagine approaching a woman in public. What is happening that causes that fear? Write this stuff down. What’s the worst case scenario? They laugh at you? Slap your face? Mock you in front of their friends? Some extreme form of rejection, am I correct?

You’re afraid, because you don’t trust yourself to handle this. You don’t have a good plan, yet. What I’ve found to work is to outline every possible outcome, analyze the nature of it, and design the ultimate response. For example:

You: Hello.

Her: Uhh, hi.

You: What do you think of the band?

Her: Are you hitting on me. ‘Cuz, uh, I have, like, a boyfriend. And he’s way hotter than you!

Now, if you don’t have a full charge on your self-esteem, then this is going to hurt you. But, take a moment to analyze this. What would you do if a girl (who was completely not your type) put herself out there and approached you? I’d hope that you’d treat her with dignity and respect (as you would like to be treated)? You wouldn’t react in any of the negative ways that you imagine being treated when you approach someone. Please tell me I’m not wrong.

What’s the perfect response? I’ll get back to this, later on.

cont. in next message.