# Dating again



## leste

Hi, I’m new here. Is a dating/sex topic okay to ask?

I’m 34. Last December I met a guy the old fashioned way and we’ve been steadily getting to know each other. We have lunch together every weekday now, and we’ve gone out 12 times between January to now. We haven’t had sex, nor gone past making out. Besides kissing I’ve only ever been with one man. I haven’t had sex in 10 years. 

He hasn’t pressured me at all and hasn’t had any qualms about going more slowly than the norm. He invited me to his house for dinner on Wednesday, and I think I’m ready for that but I’m nervous as all heck. We are both off for a few days and we are both kid free those days. I haven’t spent the night with him yet. He’s a really great guy. He’s very attractive and I want to go further with him. The nerves are holding me back. He knows that I’m nervous and said we can do something else instead of going to his house, but I think I’m ready to take that step with him. 

I’m nervous because I don’t know how it will go or will be with a new person. I have only been naked with one man, and I’m nervous this guy won’t find me attractive. I’m in good shape, and clothed I’m confident in my body. I’ve only shared my body with one person though and, like everyone, there are things that I am self-conscious of. I’ve had sex before but it’s been 10 years and when I was having sex it wasn’t very good. My experience consists of one position for around 30 seconds each time… That’s just how it was. I have zero experience with oral. I’m nervous about not being in the loop and being unsure of what is and isn’t okay or expected. Having sex with a husband might be different than someone I’m dating. I don’t know? I’m nervous that it will hurt because it’s been so long. I don’t want to make a fool of myself. I want him to take the lead but I don’t know if he will. I know times have changed but having more than one partner wasn’t what I wanted. I still feel like I’m cheating too. 

If we have sex and the first time is bad, is that a deal breaker for guys? Is being inexperienced in my mid-30’s a deal breaker? He knows my relationship history, but he doesn’t know that I haven’t had sex in 10 years. That’s not something that I tell people. 

Is it normal to be this nervous? I think I’m ready to do it. It’s hard for me to let someone in. I’m tempted to break off the whole thing instead of facing my fears. 

Even just wearing his bunny hug when it was cold out was a mixed bag. Does being with someone else ever stop feeling weird?

Should I tell him why I’m so nervous or is that a bad idea? 

I don’t want to make a fool of myself or be hurt.


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## Betrayedone

Oh boy......First thing? Relax......It's going to be ok. You're fretting too much. You have explained your concerns very nicely which is good. My first piece of advice is to NOT do anything your are not ready for or comfortable with at this point. You need to make sure this guy is the real deal and not just a smooth tongued slicky boy. Make sure to the best of your ability that he is really interested in you. You don't have any idea what his experience level is I am guessing. You might be a good match! Somehow, to the best of your ability, you need to let go of your negative body image and view your body as an asset, not a liability. That negative image will hold you back emotionally. Take your time, proceed slowly and enjoy yourself. Trust your gut.........Others will chime in shortly with more advice.


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## notmyjamie

As a 51 yo women who with my STBX for 25 years I can completely relate to what you're talking about. I was talking with a friend the other day who was pushing me to start dating. I said I felt like this alien from the Star Trek series. She was an empath who imprints on her husbands needs and desires and that's all she does for the rest of her life. I know what my husband needed and desired and I'm not sure I'd know how to do anything different at this point. 

He told me the only way to change my mindset was to start dating. Just do it. "once the first time is out of the way it will get easier" was his exact words. He divorced his wife after 15 years together so he knew some of what I was talking about. 

If this guy has lunch every day and has been dating you since December, I'd say it's a good bet he is invested in you. He already knows your anxious and nervous about being with him. I think telling him why might be a good idea. Tell him that it's been a long time, your only other partner was not very creative and so you're worried that you won't know what to do to satisfy him. Be honest, tell him you're feeling almost like an inexperienced virgin. If he's worth his salt at all, he'll tell you that it's fine for that to take time. I don't think people expect someone to hit a complete home run sexually on the first time. You are only 34 years old, you have time to learn what he likes and learn new things with him. After your experience with your ex, I think you might even be pleasantly surprised. If you're nervous about oral sex, there are literally thousands of website to give you advice on that. Do a google search but keep in mind, all men are different and you will have to keep his likes and dislikes in mind as you progress along. Tell him you want him to tell you what he likes. As for oral for you, there is nothing to be anxious about there...he'll be the one doing all the work. As time goes on you'll learn what you like and don't like as well. 

As for being insecure about your body, I'd suggest leaving the lights off the first few times until you are truly comfortable with him. I doubt it will hurt much unless he rushes things. 

So, go, have dinner, enjoy a glass of wine (if you drink) and that might help calm your nerves a bit. But just one, you don't want to be drunk. Once this first time is behind you, you'll feel much better about it...or so my friend swears to me LOL


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## StillSearching

leste said:


> Hi, I’m new here. Is a dating/sex topic okay to ask?
> 
> I’m 34. Last December I met a guy the old fashioned way and we’ve been steadily getting to know each other. We have lunch together every weekday now, and we’ve gone out 12 times between January to now. We haven’t had sex, nor gone past making out. Besides kissing I’ve only ever been with one man. I haven’t had sex in 10 years.
> 
> He hasn’t pressured me at all and hasn’t had any qualms about going more slowly than the norm. He invited me to his house for dinner on Wednesday, and I think I’m ready for that but I’m nervous as all heck. We are both off for a few days and we are both kid free those days. I haven’t spent the night with him yet. He’s a really great guy. He’s very attractive and I want to go further with him. The nerves are holding me back. He knows that I’m nervous and said we can do something else instead of going to his house, but I think I’m ready to take that step with him.
> 
> I’m nervous because I don’t know how it will go or will be with a new person. I have only been naked with one man, and I’m nervous this guy won’t find me attractive. I’m in good shape, and clothed I’m confident in my body. I’ve only shared my body with one person though and, like everyone, there are things that I am self-conscious of. I’ve had sex before but it’s been 10 years and when I was having sex it wasn’t very good. My experience consists of one position for around 30 seconds each time… That’s just how it was. I have zero experience with oral. I’m nervous about not being in the loop and being unsure of what is and isn’t okay or expected. Having sex with a husband might be different than someone I’m dating. I don’t know? I’m nervous that it will hurt because it’s been so long. I don’t want to make a fool of myself. I want him to take the lead but I don’t know if he will. I know times have changed but having more than one partner wasn’t what I wanted. I still feel like I’m cheating too.
> 
> If we have sex and the first time is bad, is that a deal breaker for guys? Is being inexperienced in my mid-30’s a deal breaker? He knows my relationship history, but he doesn’t know that I haven’t had sex in 10 years. That’s not something that I tell people.
> 
> Is it normal to be this nervous? I think I’m ready to do it. It’s hard for me to let someone in. I’m tempted to break off the whole thing instead of facing my fears.
> 
> Even just wearing his bunny hug when it was cold out was a mixed bag. Does being with someone else ever stop feeling weird?
> 
> Should I tell him why I’m so nervous or is that a bad idea?
> 
> I don’t want to make a fool of myself or be hurt.


Your history is welcomed by most men, so don't worry. You sound a lot like my current girlfriend. I was married for 25 years prior. She had not been with a man in years. Are you open to having him teach you what he likes? Are you open to oral?
"If we have sex and the first time is bad, is that a deal breaker for guys?"...not at all if your open to try new ideas.


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## jorgegene

If he's the right guy, it won't be a problem.


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## wilson

Don't make a lot of assumptions about what a good sex partner needs to do or what sex acts are required. Think of sex like pizza. Is there only one kind of pizza that's good? Probably not. Even you have a favorite, you like a lot of different pizzas. So don't think you have to do sex acts A, B, and C to be a good partner.

One thing that might help you get more physically comfortable with him is to do activities where you're physical but not in a sexual way. For example, dancing, sitting in a hot tub/sauna, laying together in a hammock, and so on. This will allow you to enjoy the pleasant feelings of his touch without worrying where it will lead. This can make it a lot easier to transition into more intimate activities if you're already comfortable and enjoying his touch. It won't be such an abrupt leap into sex that way. It will more of a smooth transition where things just move to the next level naturally. And it is totally acceptable to just sleep together. That's another good way to enjoy his touch and get closer.


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## Lila

Have you two had the exclusivity talk? Is he seeing anyone else?


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## leste

Thank you for the advice. I feel a bit better.

I think he’s a good guy and I let my own fears get in the way. He knows why dating is hard for me and is understanding and respectful of that. He has gone so slow and hasn’t put any pressure on me. He hasn’t wavered when I’ve pulled back at times. He’s incredibly understanding, patient and kind. My friends have met him and like him. He invited me to his family Easter dinner on the 20th, and that feels big. Our kids wouldn’t be involved but I’d be meeting the rest of his family. His kids will be with his ex that day and my kids will be with their paternal grandparents. His parents live in a small village and for Easter they do an egg hunt and activities for all of the village kids and a BBQ. That is on the 21st and he invited me and my kids to that. I haven’t decided on that yet, introducing my kids is a separate issue, but to me that says he isn’t playing around. 

We have talked about dating history and our marriages, but not numbers. When his marriage ended he had a lot of casual sex for the first year. He realized it wasn’t healthy and took two years off from dating and sex. He had been dating for 10 months before we met. He stopped seeing anyone else in December. We are only seeing each other.

I want him to teach me what he likes because I have no clue what I’m doing. When I kiss him he puts my hands where he wants them and that has helped me learn what he wants me to do when I kiss him. I hope he will do that for other things too. I haven’t done oral before but I don’t have anything against it. 

It makes sense that the first time will be the hardest. I hope it gets easier. I like when he touches me but I tend to feel guilty for that. Being close to him feels good and weird at the same time. I want to get more comfortable with him. I like the suggestions of doing more things physically that are not sexual. I have avoided doing things that would easily lead to sex because I haven’t been ready. I don’t think he would be upset if I go over for dinner and we don’t have sex. I don’t want to lead him on though. I should be able to talk to him about it. He’s easy to talk to and he’s been nothing but supportive. At times when I’m kissing him I feel like I’m cheating, among other things, and I don’t want that to be on my mind while having sex with him.


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## uhtred

It sounds like he cares about you, so he is almost certain to think you are attractive. (if he doesn't, kick him to the curb...). Seriously don't worry about that, affection / love provides wonderful rose colored glasses, but I suspect he doesn't need them with you.

Sex - don't plan. (other than birth control of course). Do what seems right at the time. No need to worry about what you will be doing in advance, do what seems good when its happening. Its great if he tells you what he wants, but don't be shy about telling him what you want either. 

If both people are trying to please each other, sex will be good, even if specifics don't work out the way you want.


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## wilson

You might want to read the book "The Joy of Sex". It's a pretty good book for couples who want to explore sex in a loving way. It goes over a lot of the variety of sex, so I'm sure it will have a lot about oral sex and everything else you wanted to learn about.

As a bit of humor, do any of you remember a long time ago when Chevy Chase was on "Saturday Night Live" and would be on the phone at the start of Weekend Update? It was like he was having a conversation with someone else when the segment started. You'd hear the tail end of it as he ended the conversation. Anyway, there was one time where he was on the phone when the segment started and he was saying "No, I don't know why it's called that. You're supposed to suck, not blow." So that's one bit of advice I can offer


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## Lila

It sounds like he's a keeper. If he's waited this long and is introducing you to friends and family then I'm sure he'll be patient while you each learn how to please each other. 

Doesn't matter whether someone has had 100 lovers or just one, each one is unique. Communicate with your fears to him and let him assuage them. I'm pretty sure he'll be delighted to talk to you. Could be sexy too.


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## notmyjamie

wilson said:


> As a bit of humor, do any of you remember a long time ago when Chevy Chase was on "Saturday Night Live" and would be on the phone at the start of Weekend Update? It was like he was having a conversation with someone else when the segment started. You'd hear the tail end of it as he ended the conversation. Anyway, there was one time where he was on the phone when the segment started and he was saying "No, I don't know why it's called that. You're supposed to suck, not blow." So that's one bit of advice I can offer


LOL...she might be a little young to have seen that bit. 

leste it sounds like you're feeling a little better about things. I'd also guess that if he takes the time to guide you through kissing, he'll guide you through anything else. Honestly, this might be a huge turn on for him...he might like that he gets to lead things, at least for now. I really wouldn't worry about it, he sounds like a nice guy. Just enjoy yourself, it's not cheating, you have every right to be with this man.


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## Mr.Married

From a mans point of view: It is perfectly acceptable for you to tell him everything you just told us .... and he would VERY likely appreciate your upfront honesty about it.

I think you will find your 30 second days are over. 

A fantastic gateway would be to start with a nice long ..... massage !!


Bad sex as a deal breaker: Let's put it this way....the plain fact that your interested and actively seeking advice about it already makes you have very high success potential
as a partner.

LASTLY.......never be scared to verbalize what you want, what you don't want, and what you want to learn.

I PROMISE YOU HE WILL VERY MUCH APPRECIATE THE DISCUSSION.


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## Spicy

Sounds like he’s the “real deal”.

I would be totally honest with him. Tell him your concerns. It will be bonding for you both.


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## Ursula

For starters, I take it that you’re divorced? If this is the case, you’re most certainly NOT cheating. 

That’s great that he hasn’t pressured you into going further than you’re comfortable any faster. Also awesome that you guys met organically. Take it from someone who’s been in the online dating circuit for awhile, most men pressure for sex by date #3, some pressure sooner. If you’re not into this or don’t want to deal with it, I would suggest opening up the lines of communication with your current beau. It sounds like he’s a rare find, and if he cares about you, he’ll be open to hearing your concerns.

As for the actual act of sex, it differs for everyone. If you would prefer him to take the lead, all you have to do is say that to him. If he knows you’re this nervous, he should have no problem with gently taking the lead.

Bad sex being a deal-breaker for guys… I have no idea. If he doesn’t know that you haven’t had sex in 10 years, that’s information that you might consider sharing with him. 

I understand that you’re tempted to just break the whole thing off in order to not face your fears, but personally, if it were me, I wouldn’t do that. I know what men are like, so if you’ve found yourself a decent one, hang onto him.


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## Ursula

leste said:


> At times when I’m kissing him I feel like I’m cheating, among other things, and I don’t want that to be on my mind while having sex with him.


Can I ask why you feel like you're cheating?


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## leste

Thank you for helping me. I'm going to try and talk to him tonight if we both have time. I don't particularly want to text that conversation or feel rushed over lunch. It is probably best for both of us if he knows more about why I'm nervous. I don't want to scare him away, but if he was going to scare away that would have happened already. He's refreshingly honest and an open book. When we started dating he always asked first if he could kiss me, hold my hand, etc. He is careful not to overstep. He's a good guy.


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## leste

Ursula said:


> Can I ask why you feel like you're cheating?


That's more personal and I still have a hard time sharing. 10 years ago my husband went missing while working overseas. He was declared dead two years ago but his body hasn't been found. I waited for years for him to come home or for answers. I didn't get closure, and that makes me feel like I'm cheating. My son's don't remember their dad. It's hard for me to let him in all the way because I'm scared to be hurt again, to feel abandoned again, to get close to someone again then lose them, to get use to him being in my life, to introduce him to my son's, to feel like I'm replacing my son's dad, and because I've done it alone for so long. When my husband went missing I had a newborn and 12 month old twins and my family lives in SC while I was in Western Canada. The guy that I'm seeing knows all of that.


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## Ursula

leste said:


> That's more personal and I still have a hard time sharing. 10 years ago my husband went missing while working overseas. He was declared dead two years ago but his body hasn't been found. I waited for years for him to come home or for answers. I didn't get closure, and that makes me feel like I'm cheating. My son's don't remember their dad. It's hard for me to let him in all the way because I'm scared to be hurt again, to feel abandoned again, to get close to someone again then lose them, to get use to him being in my life, to introduce him to my son's, to feel like I'm replacing my son's dad, and because I've done it alone for so long. When my husband went missing I had a newborn and 12 month old twins and my family lives in SC while I was in Western Canada. The guy that I'm seeing knows all of that.


Holy macaroni, I'm so sorry that you went through all of that. I would say to just keep being open with your new man, and things will fall into place. He sounds like a real keeper to me. I understand a little more why you feel like you’re cheating, but rest assured that you aren’t.


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## notmyjamie

Ursula said:


> Holy macaroni, I'm so sorry that you went through all of that. I would say to just keep being open with your new man, and things will fall into place. He sounds like a real keeper to me. I understand a little more why you feel like you’re cheating, but rest assured that you aren’t.


I am sorry as well. My sister in laws husband went missing many years ago. His body was found eventually so she did have some closure. Sadly, the government has had to give you that closure, but it is still closure. I can understand how difficult this must be for you, but you are not cheating. 

Try to focus on your new guy and remember that you deserve this new relationship. He sounds wonderful and maybe the reason it took you so long to date was so that you'd find him. It was fated to be and you deserve it.


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