Most of us don't like asking difficult questions - we don't like putting people on the spot or making them feel uncomfortable, especially when trying to develop a relationship with someone. This is no different with someone that you met through an online dating agency than anyone else.
However, because you met through an online dating agency is probably the very reason why you should ask the difficult questions. Remember how we said that you don't have anything to go on except for the profile and the messages you have been sent? Maybe you don't ask the difficult questions straight off but after two or three messages it's fine to start weaving one or two in with each message. If they baulk at the questions then you have to ask yourself whether they're ready to open up for a proper relationship. Perhaps they have something to hide?
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Anyone who is thinking seriously about you won't mind the awkward questions through your dating agency. In some respects it can help to move things along because awkward questions which elicit full answers tend to make the bonding process quicker as you have a greater understanding of why you are both the way you are. Do remember that people do make mistakes in their lives which they may or may not wish to repeat - it's up to you to decide where you think they stand on such issues.
Asking about ex partners is OK as long as you don't push too hard. If the relationship develops you will almost certainly talk about this later. You might want to find out about their relationship with their family, although these can be more complicated than they seem. Just because someone doesn't get on with their siblings doesn't mean they can't compromise or have a great relationship with you. Sometimes there is just too much water that has passed under the bridge. At some fairly early stage you really should try to meet some of their friends. As we said before, you don't need to tell anyone that you met through an online dating agency unless you want to. There is an old saying 'Know someone by their friends' which often holds true. If you just don't understand why your new date has certain friends then perhaps it's time to start delving a bit deeper.
Next - Most online dating agencies suggest that you ask lots of questions!
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