This may not be what you're looking for, and I don't generally favor medication. However, for a personal, anecdotal perspective. A number of years ago, when stress was particularly high, I started taking St. John's Wort. In addition to taking the edge off of my anxiety, I found myself communicating somewhat more facilely particularly in random social encounters. It was a surprising and pleasant realization.
Now, as a counter-balance, in addition to lessening my anxiety, the St. John's Wort also seems to lessen my "spark" somewhat, depending on dose. I countered this somewhat by adjusting the dose, e.g. at times taking 150 mg as opposed to the "standard" 300 mg.
It's not a dramatic effect, and people still consider me plenty witty (when I'm in good form); but I do sometimes notice, particularly after it wears off, that I'm "seeing further/deeper".
The thing about St. John's Wort is that it is over the counter. It's also considered to be generally fairly benign, although you do need to be aware of potentially adverse effects on some other medication regimens. There are others to be aware of, but as an example, if you are female you should be aware that St. John's Wort lessens the effectiveness of oral contraceptives.
St. John's Wort is also noted for increasing photosensitivity in some people.
http://en.wikipedia.org/wiki/St_Johns_Wort#Adverse_effects_a...
For me, in part perhaps the St. John's Wort helps me to let go of my own concerns and to focus more on the immediate moment and what interests the other person. This immediacy eliminates much of the "hesitation" that quickly grows in awkwardness to the point where the interaction is killed.
As I've gotten older and, frankly, my hormones balance has correspondingly changed, I've found it easier to achieve this state without e.g. St. John's Wort (or alcohol, or whatever else might be used). Also, being involved in an activity that is very engaging and immediate can also on its own bypass / short-circuit / obviate this "hesitation".
So, I think there are ways to get towards what you describe without popping a pill. Perhaps meditation might be a component, over the longer term. Still, experiencing that ease is of itself interesting and informative, and so I share my experience for any benefit or further discussion it may promote.
I wish you well, and I wish you particularly the social grace you seek: As one gets older, it does become apparent how "short" our time is, and how important social life is to one's quality of life. You are right to want to improve your own.
Regards
P.S. If you do look into St. John's Wort, be sure to find a product that is standardized not only against hypericin but also against hyperforin. I've found that only those products that ensure the latter have the best efficacy for me.
http://en.wikipedia.org/wiki/St_Johns_Wort#Chemical_composit...