A
female
age
36-40,
anonymous
writes:I'm feeling anxious over a new relationship. I even feel like crying. I'm seeing a man who is 21 years older than me. Obviously, he has much more of a past than i have. He was married for three years when he was in his twenties, and has a son who is a year younger than i am. After he got divorced, he had a couple of other long term relationships. One lasted for two years, the other was four years. But he also told me that he had a one night stand when he was younger. I'm not sure if that was the only one night stand he had, but that is the only one he has told me about. He was single for 11 years, until he met me. It was his own choice, and he said he was celibate during that time. I only got my first boyfriend when i was 17, and i have only been out with a few people since then. They weren't long term relationships. They only lasted a few months, although there was one that was on and off for a while. I'm also a virgin, and i'm really worried about telling my new boyfriend this, since he is so experienced. We have been out a few times, and last time i saw him, we did some foreplay stuff ( i've done that before with other boyfriends ), and he even bought some condoms just incase we went all the way. He must have just assumed that i have had sex before, i think, and i don't know how he would react if he knew that i haven't. He has always treated me well, and he is a polite, intelligent person, but i have low self esteem and i can get depressed sometimes, so i think that's why i am so anxious over this. I don't know if i should be in a relationship with him, or just be his friend. What do you think?. I care about him a lot, but it's bad that we have such a big age gap.
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celibate, condom, depressed, divorce, foreplay, one night stand, self esteem Reply to this Question
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Fancy yourself as an agony aunt? Add your answer to this question! A
female
reader, anonymous, writes (18 February 2012): I think it would be very sad and you will always regret it if you give your cherished precious virginity away to this guy. He is a loser.
You need to learn to love yourself and find your self confidence. Keep your virginity Until then and you will make the right decision about who and when. One you won't end up regretting
A
reader, anonymous, writes (17 February 2012): I don't think the age thing is a problem really,its how you feel that counts. You have to tell him your still a virgin though, its only fair, it will make him see you in a different light, in a good way no doubt.
If you have a long relationship with any man then he will expect a sex with you too,its only natural, so he probably does think you have slept with your previous boyfriends.
Don't have sex with him until your confident you want to though and when/if your sure your ready. Only you know if you want to continue seeing him though.
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A
male
reader, Sageoldguy1465  +, writes (17 February 2012):
 Guys who are 21 years older than a young, naive girl who gets their attention are much like the fox who is hired to guard the hen house....
YOU are setting yourself up for a world-class disappointment when this "gentleman" tips his hand and reveals that YOU are targeted to be his next sexual conquest....
P.S. I love your description of his past. He SOUNDS like a regular "choir boy"..... but be careful to NOT be deceived....
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A
reader, anonymous, writes (17 February 2012): I'm going to say I don't think he is long term material.He's been single for way too long. Some men have great self restraint and self control but to say he has been celibate for 11 years is highly unlikely. I'd like to know what he deems celibate.To some, celibate just means unmarried and uncommitted. To others it can also mean taking on a 'vow' of no sex. The main use of that word historically means to not be married. So I question him on that for certain.Lap dances? Hand jobs? Oral Sex? No long term dating?Hmmmm.I personally think Dude is upselling himself to 'get' you. He wants you but not for anything long term, just sexually. If you are going to be comfortable with that and realize he may move on after he gets what he wants; then have a short term whatever with him.If you don't like this idea, cool off on the sex, and keep his as a friend. I like this route better because then you can for certain assess if he is someone reliable and does in fact value you for your friendship.Please say you are in counselling to address your 'bouts' of depression. That needs to be maintained otherwise you can make some serious decisions in a not so good or healthy mindstate. So head to a Family Doctor. We want you healthy and happy so you can make healthy decisions that will help you be a happier young woman.
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A
female
reader, So_Very_Confused +, writes (17 February 2012):
 He has no clue you are a virgin and you must tell him if you are to continue this relationship… if you care about him and he about you then I think you can try it out….
I mean nothing is written in stone, you are over 21 both single why the heck not give it a shot.
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