General Dating Questions/dating/feeling lonely


I am in my mid-thirties. I have had social anxiety and am taking medication which I believe is helping the anxiety.  The social anxiety refers to guys that I am attracted to. I have never had a boyfriend, have always had low self-esteem mainly due to my being a bigger girl-I wear a size 22 or 24. I have lost some weight-about 50 pounds. I have never ever been able to talk to guys I am interested in and have lost out on a couple potentially great boyfriends because I could not work up the courage to talk to them.  With therapy and medication, my self-esteem and confidence is improving, which is good.  I am 35 and still a virgin.  I really want to have sex, understandably.  I would prefer to be in a caring relationship with someone. I have joined a couple of online dating sites. This guy contacted me and I don't think he wants a serious relationship, just sex.  Probably a "friends with benefits" relationship.  I never thought I would want that kind of relationship where it was mainly for sex, but now I think I want to go see him (and have sex). And have a casual sexual relationship. Of course, I am lonely and want to lose my virginity. But I have thought about this for several days. My concern is that I will regret having sex after I go home-he lives an hour and a half away. I have waited 35 years and I feel like that is long enough.  I am just upset because I would like more than just sex, but I realize that probably will not happen. I am so lonely and tired of not having anyone. This may be too much information, but oh well-I use sex toys regularly, but I want a real male who finds me attractive.  What are your thoughts and advice?  Thank you.

Hi Holly,

I'm going to answer this question with some of my own experience, rather than a more psychological view. I, too, have been in this position where I had extreme anxiety and I was deeply unhappy with my body and weight. It is normal to feel lonely when you are alone but at the same time, they say it is worse being lonely when with someone than being alone - please bear that in mind whilst reading my rather drawn out answer.

I didn't lose my virginity until much later than my friends but had given up on my idea of "the one" by then. I decided that I'd date and that as I had, had some sexual experience, I'd bite the bullet and have sex without telling this person that I was a virgin. It was an good experience with no pressure and my virginity was gone, without a care in the world. I decided not to see this person again after the second time we met because it wasn't ever going to be a relationship but I don't regret it; it taught me that I was desirable and that I can be sexy. If someone wants to date you, kiss you or entertain taking you home, I don't think that your body can put them off.

Play sexy, dress sexy and be sexy by being yourself and totally loving it. (Please know that it isn't about size necessarily, when I lost weight, I was less confident than I was a couple of years before, for a long time.) A couple of months before meeting the guy I lost my virginity to, I went out and bought new sex toys and sexy lingerie and learned to love and please myself. Understanding your body is the first step to a good first time and having fun, which you are already on your journey to accomplishing. Get your hair done, paint your nails, put some make up on and preen yourself, then put your sexy underwear on and look at yourself in the mirror. Take a long look at how sexy you are, get excited about your new purchases and go to bed with your toys. See what feels good to you and work yourself into being comfortable, explore different toys with different designs, sizes, etc. Then when the real thing happens, you won't tense up and hate every minute of it. Please remember, we all feel embarrassed from time to time when it comes to being fully naked with a sexual partner, especially firsts or new ones. I recall that I would wear babydolls and lingerie that would cover my 'bad bits' but once you are comfortable with someone, being completely naked gets easier.

I'm not saying having sex with any guy who comes along is the way to go because I was treated amazingly by this man who took my virginity. However, building up the idea of the perfect partner may not be in your best interest and I largely felt like I didn't want to in a position where I knew nothing when I met my 'perfect man' because I wanted him to be satisfied sexually. I'm not saying settle for the first guy but when you meet a guy who you're comfortable with and makes you feel good, why not lose your virginity to him if you're comfortable with it? On the other hand, you may want all of your dating and sexual experience to be with one person and not having a comparison sexually or relationship-wise may not bother you. It just did for me. You don't have to tell the person, unless you want to bond over it, you feel as if you should forewarn them (but that can put people off) or you feel as if it would make your experience better.

However, that shouldn't be the be all and end all. Try some online dating, speed dating, getting your friends to set you up on dates and trying new hobbies to meet new people (doing something you like, brings a smile and joy into your life which attracts people who have the same interests but also pick up on your passion). Date a lot, be safe and learn about what you want in depth by doing so. If an online dating profile isn't working, take new pictures, change the primary picture every couple of weeks or month, as well as re-wording your profile. You are worth it, you can attract someone and you can have someone who treats you well, desires and enjoys you. You should always take the view before a date; 'what if I don't like them?' Rather than worrying about what they think about you.

To tackle some anxiety, write down what makes you anxious about dating, losing your virginity and why you feel you might want to wait, including your feelings towards these things. Then also write points for/against these things. It may help towards working out what you want.

I hope that this advice can help you and if you have any more questions please ask.

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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