Be Honest With Yourself
The first thing you have to be clear about is whether or not you really want to be sleeping with THIS person. You like him and part of you is interested in sleeping with him, but another part of you just does not seem ready. This is where you must simply be as honest with yourself as possible. Is your concern that you are not ready, or are you simply making a larger deal out of the situation than is called for? If the reason is only fear, but everything else in you says it is the right time, then it is time to squelch the fear. Conversely, if it seems like a good idea but there is a part of you that feels he is just not right, or it is too soon, and then trust that instinct.
Setting Yourself and Him Up For Disappointment
Some women create a fantasy of what a first time with a particular person “should” be like. This type of thinking more often than not leads to disappointment. Remember that first times with a significant other (or potential significant other) are often exciting, a little scary, and often awkward. You and he are trying to get use to one another and it rarely is wholly comfortable immediately. Lowering that unrealistic expectation may end up leading to you being pleasantly surprised.
How You’ll Know He’s Worth The Effort
Many are concerned that most men put on a front in order to gain what they want. This is then followed by a 180 in their personality that cannot be retrieved. Ask yourself when deciding whether he is worth it is what will it mean to you? You cannot control what he thinks for feels, but you can ask yourself how it will affect your feelings. If you are not prepared for the possible effects, then sleeping with him is probably not the best idea.
You Can Always Try the Direct Approach
Rather than deal with your own mental games and try to figure out if it is right, try talking with him. Bring him into the conversation about whether or not sleeping together is the right call. Remember to do this at a time where you are not both already sexually charged. Find time to sit down and discuss it like adults. While this may not be the most romantic approach, it is the most sincere and indicative of the healthiest relationship.