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?

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?


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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.

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    • Even though I am pretty sure there is interest but still there is a possibility that he is just not that into me and wants to stay friends. If it's just that, do you think he would start pity me for giving in too much without him reciprocating?

    • No, I don't think so. You're not giving too much, for one thing. And for another, guys don't automatically rush to pity someone who has feelings for them. That's just not what we do.

    • Thank you for your words. Now I know what my decision should be :)

What Guys Said 2

  • Maybe he took his downsizing as a real hit. Since you work for the company which fired him, maybe he has that on his mind when he sees you. I know it's a bit far-fetched, but it could be a reason why he's taking some distance. Also, he might be saving his money a lot while he's jobless, and therefore, mood + money = not wanting to date or thinking he won't attract anyone.

    Stay around like you do (once a week) until he has found a new job.

    But you could also suggest him more explicitely that you like him.

    All you want is to know where you stand, so don't hesitate to talk about it.

    Good luck :)

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    • I actually have a further question to all you guys, as above, so I copied and pasted :). Even though I am pretty sure there is interest but still there is a possibility that he is just not that into me and wants to stay friends. If it's just that, do you think he would start pity me for giving in too much without him reciprocating? Hope you can help me

    • Indeed, you haven't given lots so far, so no problem. Besides, unless he can read minds, he doesn't necessarily know you crush on him. You know, us guys are... dull sometimes, especially when we have stuff to deal with elsewhere.

    • Haha I agree that I am not giving much but I am sure he knew I have a crush on him cause he knew (since almost everyone knows actually) that I'd only go out with a guy if I am definitely interested. Yes, I am selective I have to admit.

  • Don't worry about feeling like a fool, your the only one that can make yourself feel like that. Although he may be in a difficult time in his life, offer your help. It could be from either sending him job posts to making him some cookies. If you show that you want to help him, it will make him a lot more interested in you as well as show him your personality .I know if I was really stressed and there was a women who I knew was trying to help me, I would do my best to repay the favour ;).

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    • Again, copied and pasted my further question. Sorry for this silly bit! Even though I am pretty sure there is interest but still there is a possibility that he is just not that into me and wants to stay friends. If it's just that, do you think he would start pity me for giving in too much without him reciprocating?

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