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How do I get started with her?

Tagged as: Crushes, Dating, Sex<< Previous question   Next question >>
Question - (19 December 2017) 4 Answers - (Newest, 20 December 2017)
A male United States age 30-35, anonymous writes:

Little background:

I'm a male virgin who's never kissed a girl or been on a date. Total geek, overweight, and not handsome/physically attractive in anyway. Basically no redeeming qualities for the opposite sex. I've long thought about just seeing a prostitute/escort to have my first time. Get it over with and have one moment in my life where I can say: I know what sex is like. Like at long last, the fat ugly and awkward geek finally got to know what a woman's touch felt like. He cried too during and afterwards.

However recently I've started taking a liking to a co worker of mine. We talk a lot, she makes me laugh and smile, we joke a lot and have fun. I think about her everyday. I text her from time to time, not every waking hour, but mostly knowing how she's doing. We went out to dinner and a movie once. I'm hard pressed to call it a "date" because I don't think she's interested in me the way I am into her. I feel like she might only see me as a friend, which I can live with. She's so cool.

How do I approach letting her know how I feel? Even if she is interested in me like that, how do I explain to her I am a total virgin? She's experienced and I'm a about 3 years older than she is. I fear that would scare her away that I'm totally inexperienced.

View related questions: co-worker, overweight, prostitute, text

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A male reader, N91 United Kingdom +, writes (20 December 2017):

N91 agony auntYou sound like you have very low confidence and the only way you're going to get anywhere with females is by turning that around.

Firstly, why not join a gym? Exercise classes? Improve your diet? A great way to improve your confidence is to start looking after your body more.

Start to learn more about fashion and clothing as well as a number of women are attracted to guys who know how to dress well. Buy some new clothes, try a new hairstyle and look after your skincare more if you don't already.

The main fear in males when it comes to potential love interests is rejection. The fact of the matter is, we can't always have what we want, we are going to speak to girls and get turned away many more times than we're going to get accepted and the sooner you understand that then you will have less of a problem approaching females and trying to get to know them better.

Join clubs or do activities that interest you where you can meet like minded people where you share common interests which will make it easier to get to know each other. I will add that I wouldn't recommend getting involved in workplace romances as they have the potential to turn very sour and become very awkward situations.

The final thing is: 'you don't ask, you don't get' - If you never ask girls out, you're never going to go on dates or have sex that you so desperately want. They can either say yes or no, but it's always a no if you never ask.

Work on yourself and the confidence will follow, good luck.

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A female reader, Andie's Thoughts United Kingdom +, writes (19 December 2017):

Andie's Thoughts agony auntOkay, he error are a few things here:

- you need to work on your confidence

- don't focus on weight, unless you actively try to lose it

- lots of people like "geeks"

- are you prepared to find a new job if things go sour with this co-worker? If not, keep it platonic

- it's wise to have postponed the plan to pay an escort; real sex isn't like that and it won't actually improve your life

- don't advertise your virginity, just wait until you're introducing foreplay into the relationship and always ask what she (whoever you're with) wants, likes, etc. because all women are turned on by different things

One of the biggest mistakes men make are treating every woman the same sexually and thinking appearance (theirs or the women's) is more important than personality.

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A female reader, Youcannotbeserious United Kingdom + , writes (19 December 2017):

Youcannotbeserious agony auntYour self esteem is obviously very low. This is probably what is holding you back, more so than being overweight or a "geek" (what is that even?).

Women are not nearly as turned on visually as men. The majority of women will tell you they like a "nice" man, an "honest" man, a "friendly" man. Sure, if he has nice abs and looks cute, that is a bonus, but not a necessity for most. Women tend to be attracted to personality a lot more than looks. Many women class a sense of humour as very important, together with the ability to converse.

If your weight is causing you to doubt your worth, then DO SOMETHING ABOUT IT. Join a gym if that's your bag. If not, look for some form of exercise you will enjoy. It is no good trying to motivate yourself to do something you hate. Join a walking group, take up cycling, go swimming. There are lots of options out there. Also take an interest in food and what is good for you. Learn to cook your own healthy meals.

As for this lady at work, tread carefully. Work relationships are often frowned upon by employers and, when they go wrong or run their course, can make life quite awkward.

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A male reader, Denizen United Kingdom +, writes (19 December 2017):

Denizen agony auntOh brother, where do I start? 'No' to the idea of trying to date someone at work. It will just become embarrassing.

Next, get in shape. Why not? Make yourself more presentable. Being a geek doesn't mean you can't be fit.

Next, you seem to be looking for a relationship for sex. That appears to be your prime goal. That isn't what it is about. Sex is very nice, but relationships are about sharing so much more. Do you have more to share? Do you have hobbies, interests, pursuits?

If you don't then the going is going to be tough. Being powerful and rich can be an attraction to some but it tends to be superficial and, by nature, transitory.

Get yourself in shape and find someone you can relate to, and who relates to you.

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