I'm 29 years old and have never really been in a real relationship. I have a good job, have a decent personality and sense of humour too (I'm a comedian) but I just can't seem to get a girl. This frustrates me to no end.
When I was in my early to mid 20s I used to shrug this problem off thinking that things would work out for me when I got older. But now I'm almost 30 and recently got rejected by another girl and have no one in sight. This is all while all my friends are getting married.
I see that I have ascendant capricorn which might make it hard for me to get in a relationship. I also have venus in the 8th and pluto venus square means I go after the wrong girls that are not interested in me.
What are my blockages and when if ever will I ever meet someone that I can be in a relationship with?
Any help would be much appreciated.
I see a couple issues.
Neptune on the ASC opposite Chiron in the 7th house - You have a tendency to misread cues from people and take emotional offense at slights that don't exist in reality. Your 7th house is your home of intimacy and intimate relationships, and looking across the horizon to the ASC, the outer world where other people initially come in. Because Neptune is there, you don't see them clearly, nor they you. This misreading of energy on both parties causes you to react in a negative way and internalize that emotional hurt.
Pluto square Moon very tight - Pluto is in Scorpio and square very tightly an Aquarius Moon. You mentioned elsewhere about making inappropriate comments at the wrong times, etc - and this can be reflected here. Your Aquarius Moon doesn't react emotionally in "accepted" ways that other people may respond, and with the square to Pluto, you then attempt to control the emotional climate of the moment, which NEVER works. Because Pluto is in the 11th house, this hits nearly every person you interact with in society.
Mars in the 4th square the ASC - because Mars is in Aries exactly conjunct the IC and in square the ASC, you don't come across as "bring home to mom" material. Whether it is because you come on too strong, because you attempt to control the emotional climate (and with Pluto in Scorpio, your Mars affects this), combined with the easily hurt Chiron in the 7th, you likely drive prospective partners away in this manner. Mars is also in hard square to Neptune, so there may be likely issues with drugs/alcohol also. Being a stand up comedian, you are surrounded by that sort of atmosphere. Because of your Neptune/Chiron placement, you absorb the negativity of others very easily. Being in a night club, there is a LOT of negativity there, even when the place is empty. Those kinds of places absorb it and sensitive people like you will feel it, even if you don't realize it.
Saturn square Sun on MC - a perpetual dark cloud. Sun is also in a very chaotic degree. Once in a rut, it's hard to get out.
Because of these negative aspects, you'll really have to play up the positive ones. The humor comes from the Mercury/Uranus sextile and Aquarius Moon, which gives you a super-fast mind, essential for comedy. Moon is sextile Mars - perhaps more time spent in energetic pursuits (sports, hiking, etc) will translate that negative emotional energy and vent it through physical activity. Jupiter is trine moon in the 6th and tight sextile Mars - find someplace you can serve others, perhaps using your comedy - maybe helping kids through humor.
I need to see some other points in the chart you don't have, but generally you need to deflect the negative energy into other areas of your life. If you smoke and drink, stop. Hard to do when you are in a smoky club all night, I know. You'll also have to work harder and not being "on stage" all the time. When you leave the club, leave the comedian behind. Being a comedian should be what you "do", not what you "are".
As for some of your other comments, Uranus on the ASC can give great charisma, also essential for someone who performs on stage, especially one who performs alone. But Saturn is there too in the same spot -don't take yourself too seriously, and don't assume the worst about other people, or about yourself. You don't need to lower your expectations, you need to raise your expectations about yourself.