Now this is a tough one and practically depends on what situation you are in. There can be three scenarios one is when the guy is genuinely in need of some money and you are the only one who can lend it to him at this point in time.

Second is that the guy is simply in the habit of indulging himself and cannot keep a check on his expenses and ends up over stretching himself always. In such a case it is more likely than not that he is simply taking advantage of your kindness. The third case is somewhere in between the guy is basically good but sometimes he gets into stuff that lead him to a situation where he needs more cash than he has and so every couple of months or so he has to come to you for some money.

And another thing which is important is whether you get repaid at all or not. If you get repaid then there is no cause for worry you are probably just helping him through some cash flow problems. However you must keep in mind that the amount that he asks for should not keep increasing over time which only signs at situation where suddenly he takes a lot of money and then is not in a position to repay it.

Another good way for girlfriends to judge how to deal with the situation is to get a grip on where the money is going and then act accordingly. If the money is going on indulgences then you should stop lending to your boyfriend immediately. These can be in any form and not necessarily what we see as vices like alcohol or gambling. For instance if your boyfriend has a penchant for expensive clothes which he cannot afford and still takes money from you to spend on them its a vice that he can and should live without and you should not pamper him in ways that are detriment to both of you.

If you have decided that it is a case of indulgence and unjustified spending you should take a strong stance against this and say no, no matter how uncomfortable it becomes.

Its difficult for most of us to say no and it becomes especially difficult in situations such as these when two people are intimate and spend a lot of time together. But its important to say no because maybe you are heading for a potentially disastrous situation one you definitely do not want to enter and may be even deserve. Money problems are one of the worse that any couple can hope for and they may even lead to separation. But think over it if all a guy needs you for is money then its probably better to just snap out of it. However it is equally important to recognize that there are a lot of chances of miscommunication and its best to bring it all out in the open. You should take a stance depending on your situation which would either be no more lending at all or controlled lending and be ready before hand for some uncomfortable questions and situations that will arise when you are going to make this conversation. If you think through it you will be able to come out with reasons on why this is the best for both of you and how you think it needs to be tackled now itself and not later.

Relate all this to your boyfriend in a calm manner and hopefully he would understand but if he does not you have to take a tough decision and decide whether he still is worth it.