Hi there, I am in a difficult situation and really need serious advice to make a decision that I'd not regret later. My post won't be short so please bear it with me. Thank you!
I had my first casual date with this guy I like (not official dating, just to know more about each other first but there has been chemistry for a couple of months since we first met). Right after the meet up, he was made redundant due to the company's re-org. Since then he hasn't asked me out for a second date and it's been ONLY me who initiated contacts to ask how he is doing, not very often, just once a week (because I understand the stress and just wanted to cheer him up a bit and I am sure it helped!). Even though he hasn't initiated anything, for some reasons I am pretty sure he is interested (more or less, at least as his potential date :) and surely not seeing anyone. But I assumed he is now trying to get himself back on his feet first before thinking about dating (he has always been a career man and this incident happened to him first time ever in his life).
But now, I started to feel like a fool always being the one who contacted him first so I wanted to back off until he gets out of this current situation. However, I am also afraid by doing that he would think I am no longer interested then never think about contacting me again. I am totally confused now! Do you think there would be chances that after he has solved his problem and has time for dating, he would contact me again even though I stopped contacting him? Or everything will just fade away? What should I do to not bother him during his hard time (in other word going after him like a fool while he is not yet ready for dating) at the same time still make him think I'm waiting for him to overcome this situation? Is it okay if I continue to initiate texts, same thing like once a week to check out on how he is doing or it's just not worth it?
Most Helpful Guy
I think you have a couple of options you could do. The first and most obvious, is just to keep doing what you were doing. Weekly messages, keep in touch, keep yourself in his mind, and keep an eye on how things are going with him. But make those messages a *little* flirty, and try to avoid the friendzone.
The other thing you could do, is offer to take him out. Tell him you think funds might be tight after being laid off, and you don't want to see him get depressed, so if his ego will allow it, you'd like to take him out for an evening and get his mind onto other things. Happier things.
If his ego allows it, you've got a date. And if not, at least you're going to make sure he won't forget you or stop thinking of you in that way.