Is this relationship healthy for me? What advice do you have for me in general?

I am a 33 year old male and I have been dating a 24 year old girl for 6 months. We are co-workers at a restaurant and share a lot of the same friends. Due to this, we spend a lot of time together and spend the night with each other 3-4 nights a week. The initial move came from her, she started flirting with me right after I was hired on. I took things slow and cautiously flirted back but after a few times hanging out we started having sex and staying at each other's houses.

Before I continue I should give some background information about my previous relationships and sex life. I was raised primarily by my mother who was very religious and also has always suffered from severe depression. I was picked on most of my childhood for being a "good kid" and even to this day I often find myself, just like my mother, putting other's interests before my own. I have always been a great athlete with a muscular body and a young attractive face. I often was asked out by girls in grade school and middle school, but I was too immature and awkward to act on it even though I really wanted to. In my later years of high school I started to build some confidence and I continued to have many opportunities to have sexual encounters or date attractive girls, but I still never acted on it. Obviously many people assumed I was gay, but those who knew me knew that I was just very awkward and lacked confidence in myself around girls.

The first girl that I had sex with was a 18 year old co-worker when I was 19. We ended up getting close and dated for 7 months. She was outgoing and told me of some of her wild sexual encounters she had in high school. It made me feel like a loser to tell her that I never had sex before and I was nervous about not performing well. Sexually, things did not go well. The first time I couldn't stay hard inside her even though she was giving me oral whenever I would go soft. The next few times, the same thing happened. She enjoyed making out with me and I was a generous lover so I would massage her body and give her oral to warm her up and tease her. She would beg for me to her whether I was drinking or sober, day or night, I never could keep an erection for more then a minute and for both her and I, the sex was unsatisfying. I never came with her and after 3 months of trying, we gave up on sex. It was a toxic relationship for the next 4 months. I liked her personality and she liked mine, but she and I were both frustrated that we couldn't have sex.

I went to a doctor and was told there was nothing wrong with me physically. I was in tremendous shape, had tons of energy and stamina while playing sports and in many aspects of life, but I couldn't get my to work. I can however maintain an erection and perform well during masturbation in private. I do not really need porn, when I was 17 and first started masturbating (late bloomer), It was the 90's so there really wasn't much porn to be had. I read about many men who have wired their brains so that they can only get good erections while watching porn. I do not believe this is my issue because I only masturbated a handful of times before I met my first girlfriend. I certainly was not doing it as often as my friends or classmates in high school. On average from age 20-30 I only did it once or twice a week.

In my 20's I had a couple other girls that I tried to have sex with and the same thing happened every time. Either I couldn't get an erection at all, no matter what she did, or I would have one from making out and then I would lose it shortly after we started having sex. From age 24-31, I pretty much gave up trying. If a girl was going to walk up to me and ask to have sex with me, I would obviously oblige, but I wasn't going to make an effort to seduce a girl when I assumed it would just end in frustration and humiliation. This has really hurt my confidence as a person, it makes the thought of sex or flirtation uncomfortable to me because I feel inadequate. I have felt uncomfortable around women and have had a small sample size of female friends. The female friends I do make, end up always wanting to have sex with me and I don't act on it and then they end up holding that against me and we end our friendship. I spent 31 years not telling anyone about my sexual issues and it has made me very depressed at times.

I started going to therapy and talking about it. I opened up to my older brother and 4 of my close friends about it. When I was 31, I even told a girl who I really liked about it before we started dating. We lived in the same apartment building and were both single and lonely so we slept with each other and made out a couple times a week but she refused to have sex with me because she said if it wasn't going to be good, then she didn't want it. I figured there was no point telling her it was going to be good knowing my past. I was so desperate to keep trying to have sex and see if I could solve my issues that I stayed exclusive with her for a year and a half. I know she was attracted to me and if I didn't have this issue we would have had a good relationship, but she was stubborn with the no sex policy. We would sleep naked together, spoon, give each other hand jobs, etc, but aside from the back story I gave her early on, she could see the evidence that many times, I wouldn't even get hard at all during some pretty intense make out sessions, so she was not enthusiastic about trying penetrative sex. We ended up both dealing with similar issues from the landlord that caused us to decide to move in together, mostly out of convenience (I knew it was a bad idea, but again, I was still thinking with my that so badly wanted to have good sex for the first time in my life.) The final year that we stayed together, living together, was toxic and I almost lost all of my friends. She manipulated me in so many ways and my friends lost respect for me. I lost a lot of respect for myself too, but being 32, and never getting to have legitimate sex with anyone because of some physiological issue that couldn't be solved, was already enough of a reason to make me feel low and depressed. The positives that I took from that relationship was that even though it was mostly toxic, I had a very personal relationship with a girl. The most serious relationship I had been in, and for her as well. At times I felt very comfortable with her and towards the end, I started to notice I would get really good erections waking up in the morning next to her, or even just sitting next to her watching a movie. Maybe, I am destined to only have good sex with someone I spend the rest of my life with? But is there a woman I would find attractive that would be so patient with me?

Back to my present situation. The girl I am dating now is someone who had not had a boyfriend in 3 1/2 years. I don't know if she was sexually active during that time, it is hard to tell with her, but I can tell she was pretty wild from age 16-21. She is very social and has many guy friends. I had just gotten out of that 18 month toxic relationship and had a string of bad situations happen to me financially and physically. But again, now that I am in my 30's, I feel very desperate, so when an attractive girl starts flirting with me, it's hard for me to not want to engage. I don't know if I will ever be able to change my mentality with woman, but woman can always pick up on the fact that I am a nice guy who is desperate (not a good combination). The first few times we tried to have sex it didn't go well and I was ready to give up. However, partly because she is just a very chill person and didn't make the situation uncomfortable, and partly because I continue to gain confidence and maturity, I let her know this is an issue I have dealt with, but I want to keep trying. I can happily say that with this girl I have had a couple good sexual sessions and finally have been able to stay hard and cum at the end. Every time though, I can tell she is left wanting more. She holds back from making me feel bad when she is sober, but when she is drunk, she makes many cues to show how unhappy she is with the sex we are having. Because I always want to please woman, I end up spending a lot of time doing oral on her and if my didn't work well or I came too fast, I would finger her till she was satisfied which she likes but I can tell she resents the fact that I am not able to use my .

I have seen a progression in our relationship (6 months) that has moved from us both playing hard to get and being flirty with each other, to me being overly nice, and her seeming bored with me. She used to light up when I would come and talk to her and would surprise me with hot sexual favors such as giving me oral in a parking lot. But even though we are spending more and more time together and things have progressed to us getting to know most of each other's friends and some family, I don't feel respected in the relationship. She dismisses the idea that we are dating to anyone who asks in front of us. Most guys would love the idea of an open relationship with a girl who is DTF 3-4 times a week with the ability to other girls on the side, but because of my sexual issues, I still don't have confidence that I could perform in a one night stand (never have). I often have thoughts that she is having sex with other guys, but I can't find the right way to ask her if she is exclusive with me. The same thoughts I have always felt while in a relationship go through me head, that if she is being loyal to me, I feel bad that she is being held back from better sex.

Being in a bar/restaurant scene, everyone at our work drinks a lot and we often go out til bar close. The more she drinks, the more she gravitates towards bad boy party guys who treat her and everyone else poorly and away from me, the nice guy who has a smart but dry humor. It makes me feel uneasy when I am hanging out with her and other co-workers and she is drunk snap chatting to her friends pictures with them and I am left in the dust. Her friends that see her like that all look at me with concern and tell me that I need to solve that or leave her. When I talked with her one time about us dating or just being casual she dismissed it. When she gets black out drunk, 2-3 times a month, she is blowing up my phone and begging for me to come find her. I feel good that she is always looking for me in those instances and her friends say that I am all that she is talking about when she gets like that. When she gets like that and I find her she is very horny and will try having sex with me in the bar or public place. I feel uncomfortable about it, and would never want to have a one night stand with someone who was blackout, but because we have been "dating" for 6 months, I feel it's not wrong to take her home and have sex, even if she will not remember most of it. I think of it as a subconscious bonding experience. However, most of the time, I end up getting really upset and angry at her during her blackout nights. When she is blackout and we are having sex, she seems fully conscious. I have been able to tell when she is and isn't conscious over time now. During these times, she is much less patient or understanding with my issues. She will laugh at me when I lose an erection, ask, what is wrong? What are you doing? Go, come on! etc etc. The worst of it is, that she has mistakenly called me out by other guys names during these times. The guys names always are the "bad boys", mutual friends of ours that she loves to flirt with when she is close to black out drunk. The last 2 times it made me really upset because when I was ing her, she said my name, but because I also was drunk and had whiskey , I didn't perform well, so I started fingering her. She really was enjoying it and that is when she said the other guys names. I don't think I can go on much longer without bringing this up, but I assume her response will be that she didn't mean it and I shouldn't make a big deal out of it. I am almost certain that she isn't having sex or even making out with the guys she is calling out, just that she is more attracted to them then I am when she is in that state of mind. That obviously is a big red flag and because it bothers me so much I shouldn't continue to put up with it. But, she is the first girl I have ever had enjoyable sex with, and because of my history, it is hard for me to walk away from, no matter how toxic.

I know there are woman out there that will give me the respect I deserve even with my issues. I feel that the better the relationship is with the girl, and the more comfortable I am with them, the better I perform. I also know that heavily drinking is not helping this situation at all and I need to find a girl that enjoys going out without getting drunk. But aside from all the negatives that I brought up in this frustrating rant. This girl, while sober is a hard working, charming, thoughtful person and has giving me lots of encouragement and confidence. I just don't think that we are a great fit for each other as long as drinking has to be involved but since we work together and have gotten so intertwined in each other's lives, It would be awkward for me to work with her and not be with her. Any advice is appreciated.

hi,

have you ever considered using viagra ?

I just don't think that we are a great fit for each other as long as drinking has to be involved but since we work together and have gotten so intertwined in each other's lives, It would be awkward for me to work with her and not be with her. Any advice is appreciated.

You are right, it doesn't sound like you are a good fit for each other. Each of you have individual issues that seriously need to be worked on. It sounds like you know what your issues are and that you are working on them, but it does sound like you have still work to do regarding building up your self-esteem and addressing your insecurities so as not to pick people who are likely to trigger your issues like she does. You cannot resolve her issues. However, you can make clear how her drinking is a deal breaker for you and break up if nothing changes. Breaking up is awkward no matter what. There is no way to avoid that. Next time around though, it would be best to avoid dating someone from your work for the very reason. With this one, imo, if things don't get better you need to bite the bullet and break up. If you have trouble working with her afterwards, one solution would be to seek another job.

Hi there.

I think you should stop referring to this as 'your issue'. It's not an issue and is quite common with men. I often feel for guys as there is so much pressure to perform.

As you have said yourself, it gets better as you build trust and confidence. Perhaps you're a person who needs to take things a little slower in the early days? You'll develop a much stronger mutual understanding and build all that delicious tension.

I promise you that good women would a) understand and b) work together. They would also not c) do the first two and then throw it back in your face when drunk. In some ways that is so much worse... quite manipulative.

I think it's time to break up. It'll be tough, but just maintain a professional demeanour. You'll be ok.

As for sex. Just look at it as a new skill. Like any new pursuit, you learn the basics and then build on that through practice and trial and error. And here's a tip, mistakes (and they happen all the time) should be funny in bed. A chance to laugh together, before you get right back down to it. It's amazing what a sense of humour can do for your sex life!

Some women also struggle to orgasm through penetrative sex. A man with good hands and mouth are exceptionally welcome. Get this right and the sex bit becomes a great finale... but just part of the overall experience.

Best of luck to you. I think you'll be awesome once you get a bit more confidence.

hi,

have you ever considered using viagra ?

I have in a limited capacity. When I was 19 I was able to get a trial pack and it didn't make a difference. Even though it comes with side effects I would be willing to try it but when I mentioned it to my doctor and he did a T test on me, I was told it was not going to help and I couldn't get a prescription because I was physically normal. It appears it is all psychological for me so even if viagra would help a little, it would just be a band-aid that could cause other issues. But thank you for the response.

Sorry this is happening. Alcohol is the biggest erection killer in men under 40. Even what you may think is 'social' or moderate'. And it's cumulative. You say you've had a work up and are in good cardiovascular and health otherwise. And you are in psychotherapy for performance/social anxiety.

The only area left to look at is lifestyle. Viagra works best for physiologic mostly cardiovascular ED, it doesn't counteract alcohol, anxiety or low libido from depression. Your doctor is correct. Taking unnecessary testosterone is counterproductive and suppresses your natural testosterone production.

I was 19 I was able to get a trial pack and it didn't make a difference. my doctor and he did a T test on me, I was told it was not going to help and I couldn't get a prescription because I was physically normal

I have in a limited capacity. When I was 19 I was able to get a trial pack and it didn't make a difference. Even though it comes with side effects I would be willing to try it but when I mentioned it to my doctor and he did a T test on me, I was told it was not going to help and I couldn't get a prescription because I was physically normal. It appears it is all psychological for me so even if viagra would help a little, it would just be a band-aid that could cause other issues. But thank you for the response.

Honestly, it can help. After my marriage ended, I was rather mentally broken. Also hadn't had sex in several years. When I attempted to have sex with someone new, I was also having similar issues. It was like a mental block and certainly a confidence issue. I used Cialis for a bit and it allowed me to perform and gain my confidence back. That along with getting over some of the issues I was left with after the marriage, I was back to operating normally.

Point being, they can help even as a short term solution to relax you and restore confidence as you know you will be able to perform, so you worry about it less.

Your problem won't be solved with viagra. Viagra helps if you have a medical condition that prevents you from having an erection, poor circulation, the aging of the body, etc, if you can clearly get an erection, it has to do with feeling comfortable with the woman. I think that you are just not compatible. Honestly, if i were you, i'd review my career and see if there is anything outside the restaurant business. You are just going to have successfully younger and younger women around you flirting with you up until you reach a certain age. Or have the policy of not dating anyone from work.