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General Dating Questions/anxiety,self-esteem,loneliness


I am 35 and have had social anxiety for many years. This anxiety refers to men that I am attracted to and would want to date. I also have had low self-esteem most of my life mainly due to being very overweight. I wear a size 22-24. I have NEVER had a boyfriend or relationship of any kind. I have been in therapy and taking medication which I think is really helping my anxiety. My self-esteem has recently been slowly improving. Regarding my social anxiety, I have never ever been able to talk to a guy that I like, even if I know they are interested too. I have lost a couple of potentially great boyfriends because I couldn't talk to them and/or show my interest. This has been very upsetting and painful, but time is healing it. Like I said, I think my medication is helping to lessen this fear. I am not as scared to talk to men now, but I am a shy person in general. The main problem that is very painful is that I am still a virgin at 35. I have only kissed one boy when I was 15, no fooling around. I so much want to have sex and of course I am very lonely.  Two months ago I joined a dating site. I also live in a smaller area and it is hard to meet available guys. This guy contacted me a few weeks ago and he called. I realized right away that he wanted to have sex on the first date and I am pretty sure he just wants a "friends with benefits" relationship or maybe just a one-night stand. I have never wanted a relationship with just sex, but I have been thinking about this a lot. I am thinking about going to see him and spend the night and have sex. I am 35 and I really need to have sex already and I think I could do this and not regret it,at least not entirely. I know this sounds like desperation and I guess it probably is. I do use sex toys often, but I want the real thing and to be wanted and feel desirable. I feel like I really don't want to wait any longer. I don't have any other prospects right now,either. Can you give me any wisdom or thoughts or advice?  Thank you so much!

Holly, stop where you are.

Do not go on this dating site any longer and do not meet this man. If you are aware that he is just looking for a friends with benefits kind of relationship, why are you lessening yourself to something like that? I suggest you reevaluate your self-worth and slowly start developing a loving and beautiful image of yourself, or else you will enter yourself in destructive relationships. My next advice for you is to sit down and think about what it is you want. Do you want a boyfriend or a husband? If you want a husband, something more committed and serious, you should start looking for him, because he's looking for you. Think about what is important to you in a life long partner and write it down. Keep thinking about it and start heading out there to meet new men. Find out if there are "speed dating" nights in your town where you can meet new men, or ask friends to set you up. Your social anxiety is just a result in you not dealing with the anxiety in the first place, which is why it has now led to the outside world. The connections are not relatable to you anymore since you do not have many relationships in the social world.

I suggest the best idea for now is to TRY and get started on this journey. If you don't ever try, you might get yourself stuck in darkness when in actuality, all you want is light!

G-d Bless.


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I can answer almost everything. I am religious person who strongly believes in G-d. If spiritual guidance is also something that you are seeking for, then I am careful and competent in that region. I am also very aware that it's hard to ask for help, with that being said, I am sensitive to others feelings and have gone through hardships in relationships, which demonstrates a quality of empathy and consciousness when it comes to everyday dating situations. I can answer break-up confusions/confusions in dating in general. I can NOT read minds and can answer to the best of my ability in regards to the detail you provide me. With that in consideration, please do not send me pages of information. Pick the most important and effective way to explain the problem and we can make this our problem and our solution together.


I have been in confusing relationships. Most of all I was in a 5 year relationship that really helped me in developing my intellect and sensitivities, which also played a huge role in discovering myself and those around me.

Chai Life Line; deals with special needs children

Bachelor of Arts in English Literature Certified teacher in Canada; recognized internationally

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