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Sometimes you just have to put yourself out there. A lot of girls don't realize how shy the average guy is. In fact I believe that there are more shy guys out there than those who aren't.
I've explained this time and time again, when it comes to guys you really need to be blatantly flirtatious. If the conversation is too casual, then he'll think it's no more than casual conversation between friends and won't make a move even though you're hoping he does.
It's also important to note that guys aren't the best at picking up subtle queues, so you have to make sure that what you say and how you act go hand in hand. Make sure you don't only make subtle flirtatious gestures, but also speak in a manner that shows him you're interested. Laugh at his jokes, look at him as though you're hanging on his every word, hell, it seems that you have no problem asking to 'hang out' just neither of you set a date. If he says you should hang out sometime, be proactive and tell him when you're free. This will tell him that you are interested and if he is too, then he'll agree to 'hang out' on one of the dates. If he's busy, he may tell you that they don't work for him and if he's really serious about going out with you he'll want to set something up for after that, or he may even offer to change his schedule to accomodate it. If he offers, accept, if you don't he may take this the wrong way and think you were just trying to be nice.
The key here is trying to get an actual specific date out of him. Don't let him say, maybe next week, or some kind of indefinite period, when it comes to making dates, make a date and stick with it. Even in the event that they have to cancel on you, if they are truly interested they'll offer an alternative time. Now you can sort of feel it out, usually they'll recommend a specific day in the coming week, but if they don't you now have to kind of feel it out. As time passes you'll be able to draw a conclusion. If he's constantly rescheduling, being evasive, or trying to avoid you, you know he's not interested.
The one caveat to this is that with busy men, sometimes work just gets in the way far too much to really see someone, and even though you want to, you just can't. After a while you might just want to try asking him flat out if he's interested in you to provide closure. Closure is always good because it prevents you from thinking about it for the next 5 weeks in which time you may have missed out on meeting someone else.
The good news for you is that you're 8 years his junior, guys love dating younger women because they feel if they can get a younger woman (with some exceptions) because it provides confidence that he still appeals to a wide range of women, and I don't want to make it sound like we're pigs but when it comes to first impressions, a more youthful appearance is generally more attractive.
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