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A little background. I'm 30, single and live in the suburbs near Los Angeles. I've never really had much success dating partly because of lack of effort and an underlying lack of confidence.
I've tried using OKcupid awhile to talk to women and possible get some dates. The few I've went on never really worked out at all. I've done this now on and off for several years. I have tried offline to take things to the next level but I never get any traction.
I'm kind of a geeky guy and overthink many things to my own detriment. I feel I don't elicit much sexuality and therefore not much attractiveness. I'm a pretty normal guy in that there is nothing I feel would dramatically set me apart negatively from other guys my age. I have a decent job, went to college and rumor has it that I've been known to be funny every now and then.
Recently I received a message back from a girl that I really like based on her profile info and picture. I suggested we meet and she suggested we skype. I agreed and we skyped for the first time. We talked about pretty low key stuff about our work, hobbies, what we do on our free time, drinking and social habits. Things seem to go pretty well as the conversation went pretty smoothly and after about an hour she ended the conversation but actually asked me what my schedule was like to speak next and she actually asked about my number.
I had intended to do both but she asked first. I messaged her the next day with a time to skype again this weekend.
Everything sounds good except mentally despite the fact it appeared to have gone well I'm beginning to have self-doubts about where to take this moving forward.
This isn't the first time I've felt things went well. In fact they almost always seem to me that they do. However I think I have a problem just keeping things to friendly and not digging deeper. I've tried to go online to seek some advice about this and one of the things I believe to be true is really finding a way to connect emotionally. Now every time I have an opportunity with someone I like I try to adapt this to try to take things to the next level.
I can't say things have improved over time but this is the first time I've ever skped with someone on a first meeting. I'm now more clueless than ever about where to go. Since I do like her how and when do I ask to make that move to meet in person? How should the flow of conversation go online when we have that artificial distance between us? Can some people share with me how their skype or digital communication experience went?
I don't want to be too forward about meeting for fear of rejection but maybe that's what I need to do? At the same time I feel some obligation to ask rather than wait for her to bring it up. I want some more advice than just go with the flow. I want a way to have a bit more control of the situation, but how?
Reading your post, I am struck by how much it is filled with timidity and self denigration. First things first, I get it that not every guy in the world is a supremely confident and outgoing, but you really do need to work on your self esteem and self confidence first. You are 30 years old, and the way you view yourself really does rub off on others. Your last paragraph says it all, you don't want to be too forward with her for fear of rejection.
You really do need to set up a time to meet in person next, not on Skype. I can understand her wanting to do it the first time instead of meeting right away like you apparently wanted to do. But what I would have done after the first skype chat was to invite her out to meet in person, not schedule another skype chat. This quickly weeds out people that aren't really interested in meeting people online, but just like to string along people with 'safe' video chats and endless text messages.
Wouldn't you rather find out now whether she's truly interested in you, instead of months from now when all you've done with her is endless skype chats? As always, a guy's interest level in a woman doesn't always mean that the girl in turn likes the guy.
Here's how you could have a "bit more control" of this situation: When you reply with your upcoming schedule and find an evening or few hours you're both free, suggest a place to meet instead. Ask where she would like to meet you. She won't be able to say she's busy if she actually wants this to go anywhere. If there's any excuse not to meet in person at that time ("my dog is sick"- "my car just got totaled"- "I can only Skype, I actually don't own any pants") then you'll have your answer.
For starters, take some pressure off yourself. Your goal is not to manipulate someone into connecting with you, that defeats the purpose. I think too many people beat around the bush early on instead of clearly expressing who they are and what they're looking for. You have no obligation to do anything except act like yourself.
I will say, regarding my recent experiences with women; they appreciate assertiveness. I had one girl tell me that she's sick of guys dating her and acting like one of her girlfriends. She's said she misses all those masculine characteristics that men used to have but that society now discourages. She got more specific but I won't cover that now.
Two people either naturally connect or they don't, at least that's what I've found. So just be yourself, be bold and for heaven's sake, don't be one of her girlfriends.
Well, OP, has she responded to your suggested Skype date suggestion? Do you even know if she's still interested?
If the Skype date comes to pass, you can ask her at some point if she'd be comfortable meeting for coffee. That indicates definite interest, while leaving the ball in her court, i.e. without pressuring her. That's the best you can do, at this point.
If she drags out the Skype dating beyond another session or two, you can only figure that she's not seriously interested in dating, and move on. But don't get ahead of yourself here; don't get into ruminating on worst-case scenarios. Just take it as it comes.
And be funny. That helps. . It should come naturally, which, by your self-description, it apparently does occasionally.
And be funny. That helps. . It should come naturally, which, by your self-description, it apparently does occasionally.
Yeah, this is a biggie. Humor reveals a lot about a person. We all have our own style of humor that offers a big window into who we are. And don't force it. People have good b.s. detectors. And if she responds well to your humor, keep her around. If not, ugh. People with no sense of humor are a miserable lot. Avoid at all cost.
You’re overthinking which means you’re trying too hard. Take a breathe and have your brain move on to something else. Then the next time you talk with her just have your brain pick up from last time.
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. It should come naturally, which, by your self-description, it apparently does occasionally.
