Should you date that guy? Is he the right sort of guy for you? Are you ready to date anyone? Are you looking at this objectively and sensibly? I get a lot of people come to me for help because they started to date a guy they did not know, someone who they only knew very briefly and vaguely, some of them should have waited until they got over their ex or their own inner problems (a lot of insecure and needy women look to date for all the wrong reasons and then drive their guy away with their nagging about how he must prove he loves them and cares about them and forever remind them he loves them) and you also have people who are whole and sorted but who choose a potential partner in all the wrong way. By their looks or because they are single without looking at the other things that matter a lot.
Before deciding yes or no when asking yourself should I date that guy? Firstly lets look at the bit about are you whole. If you have recently got over a break up are you truly over it? If it has just happened have you even started to heal and understand and get to where you need to be to start again? If you are lonely and needing someone to make you less bored or lonely or to give you a boost of confidence this is not the way to go, it can not only waste your time and theirs but cause emotional problems.
When asking yourself should I date that guy you may need to speak to someone like a counsellor, an online agony aunts advice columnist, an online cheap psychic email reading might be best really are before you can go forward thinking of another relationship of any sort, even if very casual. If you are still hurting this is probably the case. If you still do not understand where it went wrong this is definitely the case. For those who are lacking confidence and needy remember this can drive people away.
Constantly seeking reassurance is draining and boring to the other person. They feel they are forever working hard at pleasing you instead of having a relationship or fun. They do not want to be your therapist. This is the problem. People get a new lover or date and they say to them look I need a lot of reassurance and then they think they can dump it on this man to provide it. As if it is all down to him to make them feel alright. In actual fact you must be whole before you can get this guy to like you and care about you and respect you, if you present yourself as a damaged ornament that wants superglue you will push him away. He is looking for a good relationship not one which is draining and time consuming with negative energy. He should not have to repair someone first before he can have a good relationship with them and he is not qualified or experienced with these things, he has no chance of being able to. He may be an accountant, he may be a shop assistant, those are his skills, not therapy. Even if you did somehow meet a therapist who was keen it would not be good to date him, you must keep the two things separate. When the lines blur it all goes wrong.