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General Dating Questions/helping a guy with his self-image, inexperience with dating


Hi! I am 37 and just began seeing a man who is 42. We are both a little shy, but I have noticed that he doesn't seem to have a lot of self-confidence in general and he has not dated very much at all, ever. But he is a very sweet guy and has a big heart.  I haven't dated a ton, but I have had a few relationships and have had sex. Whenever I bring up the subject of sex and/or previous relationships he becomes really uncomfortable. He cuddles but I initiate kissing.  We have only been on a few dates so far. Four.  I suspect that he may be a virgin, but I don't want to ask him at this point since our relationship is still pretty new.  My questions are:  How can I help him to understand that he is lovable and desirable?  If it turns out that he is a virgin, how can I teach him about sexual techniques without hurting his feelings?  I know if this happens, if this will be his first time, that he will be very nervous and anxious, understandably. I want him to please and satisfy me but don't know how to phrase it. I have some thoughts and ideas, but would like your thoughts as well.  I enjoy sex and have a healthy sex drive and I would like him to enjoy it too and feel comfortable.  How can I encourage him to give me oral sex if he hasn't done it before?  Your advice and thoughts are greatly appreciated, and thank you for your time.

Hi Holly,

If you really like this guy, take your time. That's him proving to you that he doesn't just want sex and you should mirror that if you do want more. There's nothing to say your needs shouldn't be satisfied, whilst I'm sure most people prefer intercourse with a partner, there are ways of your needs being met whilst you're getting to know this guy.

Leave him notes telling him how wonderful and sexy he is and make sure you tell him at least once a day how attracted you are to him. If you say it enough, maybe he'll absorb it.

It's about mutual want for the next step. There is no wrong and right way to deal with this situation but so what if he is a virgin? No big deal. I look at it in the way that you can both go on a great journey of exploration as he may be more open to trying new things because everything is new anyway.

Read an in depth sex book with illustrations and tips aimed at couples and leave it out when he's next at your place. Let him 'find' it when he's alone and he might just get the idea. As a virgin, you can guide him to your wants and likes and he can then tell you what he enjoys and doesn't. In terms of him getting to have oral sex with you, lead the way and perform it on him first maybe? If you don't want to do it then I wouldn't expect anything from him but showing that you enjoy his body will make him more open to exploring every inch of yours.

Don't push him, but when you do first have sex don't expect it to be great. From then on will be a great learning curve. Be open with him and talk about it is the only way to enjoy sex fully.

All the best!


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I can answer questions on how to meet people, confidence, what to do for the best dates, problems within relationships, how to interact with your partner and how to end relationships amicably and politely. More specifically, I am best at answering issues pertaining to trust, honesty, openness, fear and communication within relationships. It is important to know that everyone loves differently and we must first identify how a partner (or prospective) partner loves, in order to understand them. I cannot answer questions on whether or not someone sounds like they are interested, people are all different when they like or do not like people. I cannot tell you how someone may react or how a situation will end but merely offer you my advice on the subject.


I do not have professional experience in the area but my knowledge of psychology, teamed with forever being an agony aunt when it comes to relationships means that I have answered many questions on relationships and am proud to say I have seen quite a few relationships flourish with my advice. I am used to surveying people and guiding them in my daily working life. Due to this, I can read situations very well, often putting a much needed outside perspective to good use.

BSc (Hons) Psychology

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