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TherapistJen, LCSW, CPC
Category: Relationship
Satisfied Customers: 3777
Experience:  Licensed Clinical Social Worker and Certified Professional Coach
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Ok so I'm a 30 year old man, I've only ever been in one

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Ok so I'm a 30 year old man, I've only ever been in one relationship and only had the one sexual partner. This relationship lasted a little over 4 years and I have been single for the 6 years since it ended. Having recently turned 30, it's triggered a little soul searching and I've realised that being single is something I need to change but in honestly I feel entirely lost and don't really know what to do next?
I signed up for online dating but in honesty I'm intimidated by the entire prospect and massively afraid of the rejection I know is about to occur repeatedly. So having signed up I haven't really spent much time messaging people. I did message one woman and after 2 weeks of messaging back and forth did manage to get a date out of it. However after the first date we arranged a second date and she continued to initiate communication on a nearly daily basis however on the day we were to meet up for the second time she cancelled on me at the last minute, she was very apologetic and did attempt to arrange a reschedule. Unfortunately I was busy on the days she offered to reschedule for so we agreed upon doing something the following week(this week). So this morning I asked her when she is free to meet up this week but I have yet to receive a response. We've been messaging back and forth now for over a month and she initiates communication on a near daily basis which I was kind of assuming meant she was probably interested in me. But since she cancelled the last date we arranged and now appears to be ducking my question regarding reschedule I'm beginning to wonder what's actually going on?
To be honest I assume from her perspective I may not appear to be all that interested. I am pretty lacking when it comes to women. Women are quite literally alien to me, all my friends are male and have been my entire life, I grew up in a household where the only female was my mother, I work in an office with only other men, I can quite literally go entire weeks without interacting with a woman at all. This lifestyle has left me scared of women, especially ones I find attractive, logically I understand that I should have no additional difficulty interacting with women than men but in real terms I struggle. What's worse is I have no clue how to "date", and I have a complete inability when it comes to things like flirting.
So I guess my "question" is what do I do next? How do I "fix" myself so that I can actually date women and find someone?

Thanks for being so open...first thing that seems important for me to say is that you don't need to be fixed....possibly embracing your gentle nature and not beating yourself up for how you are in the world. This dating thing and online world to do so can be very scary and intimidating so just know you are not alone in that and many people with whom you interact might be going through all that you are. The key to negotiating this is to have an open mind about it all and know that not everyone will be for worry about the rejection piece, which of course is normal, but let's not forget you might not be interested in everyone either. Try to message a few women, take your time, don't reveal everything all at once and schedule some coffee time, drink time or dinner time. Prepare to feel uneasy about's new to you and that is okay. In terms of this woman, I would reach out again maybe tomorrow and let her know you are still interested in meeting this week and hope she feels the same and to let you know either way. A thick skin while doing this dating thing is needed...doesn't mean to harden yourself to the experience, only to know that there may be some good experiences and some less good....but what's the alternative? It can be to be on your own and if that is your choice, that is fine too, but I am not hearing that, so it may take you some practice and patience and feeling uneasy, but you can get through it. Like anything new, it can take some time to adjust...give yourself that time and flexibility.

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