Dear Diary (Week 22),

I'm really bothered by how awkward and shy I’m around men I don’t know. I have a hard time starting conversations with people in general, let alone men. I don’t like approaching men for fear of saying something silly. But it’s more than that. I feel like a man who’s interested in me can at the very least approach me, one way or another. I mean, ideally, a man would come over to me and strike up a conversation. But if he can’t find the courage to do that, he should at least contact me on social media or something. It seems like nowadays women are expected to approach men, just as much as men approach women. But why?! Why can I no longer expect chivalry? Why can’t a man initiate in the beginning?

I feel pressured to start conversations with men at parties. I have these thoughts that I’ll lose my opportunity to ever be with a man I like if I don’t initiate. Another part of me feels that if things are meant to be, they will happen. But then again, that first voice tells me that while this may be true I must still take advantage of my opportunities. I’m confused, distressed and anxious about this. I often wish that I was less socially awkward and had more confidence to approach cute men at parties. But I truly feel that it’s not my style to do that. Is it something I have to push myself or is it acceptable to think that men should usually take on the role of merely initiating things with me? 

Knowing myself, I feel like I need a man with confidence and guts. A man who is going to be able to “handle me”. I may be shy when it comes to meeting men and making small talk at parties but once I feel comfortable I have a lot of “personality”. Am I wrong to assume that if a man who’s actually interested in me isn’t courageous enough to introduce himself to me, he most likely won’t be confident enough to be in a relationship with me? It’s possible that I would be better matched with a man who’s shy, though. Meaning, maybe I should initiate conversations with men. I don’t want to approach men but am I missing out by not doing so?

I may not have much to lose by approaching a man but unless the setting naturally presents itself to me (for example, we literally bump into each other), I really don't feel comfortable doing so. I make an effort to put myself out there by going to parties, for example. I don’t expect a man to line up at my door waiting to meet me with chocolate and a teddy bear (that can be reserved for a later time) but to walk across the room at a party to get to know me or at least say hi. Do I have unrealistic expectations for still expecting an old-fashioned, men approach women approach?

Love,

Faigy