Kitov – in such a situation, I would recommend possibly limiting the amount of dating but not cutting it out altogether. This can mean taking breaks, or only going out once every month or two or only going out if it sounds very shayich.
For a guy in that situation (and possibly even a girl), I would recommend considering the possibility of therapy and/or speaking to a dating coach and/or sitting down and trying to figure out if there is a reason he is not married yet. There doesn’t have to be a reason, but there often is (at least for guys). The reason may not be something that they can do anything about, but on the other hand it might be.
Some possibilities are:
1. They may have some emotional issue that they can work out by going to a therapist.
2. They may be going out with the wrong type of girls. Maybe they need to make it clearer what they are looking for. Maybe they need to move to a different community. Maybe they need to do something different in order to get set up with the right type of girls.
3. Maybe they have a middos or personality issue that they need to work on.
4. Maybe they are too close-minded about what they are looking for and they should be more open about who they go out with.
5. Maybe they say no too fast and don’t give things a chance.
6. Maybe they need lessons in dating.
7. Maybe they have a fear of marriage that they need to find a way to work out.
8. Maybe they don’t want to get married badly enough, and they have to think of a way to change that.
9. Maybe they are not happy enough or have gotten too mellow over the years, and they need to change or add something in their lives to change that.