How to help a socially awkward person?

If he is meeting women online….one thing springs to mind.

Have you seen his profile? Is he honest w/ what his interests are? Does he post a pic or just a desciption of himself? Is the description accurate?

I know this doesn’t address you exact question…but I just thought I would mention it….

Perhaps he should get involved with an activity that he likes, where he would be more relaxed and perhaps meet like-minded women.

Cooking classes
Bridge
Round or swing dancing
Skiing or golf
Volunteering somewhere other than at old-age-homes.
Church or Synagogue.
The word “date” makes middle-aged folks break out in hives.
Pet training course.

Think about group activities that you could do together, if you’re really invested in his success. Being around at least one familiar person while meeting new people can take some of the pressure off.

Until he meets a woman who is willing to tell him why she wouldn’t call him back, he’s not going to get it. Also, would you describe this person as socially inept, or lacking confidence in all situations? I would say that they are two issues, perhaps related. Has something happened to him in a relationship that makes it easier for him to sabotage romance before it has a chance to happen? Has he been scorned so badly that he feels like he will never find love again? I suspect that there are many other issues at work rather than just feeling awkward in dating situations. I don’t know that there is really a way to help somebody in his state, it’s that he needs to get his legs underneath him right now, recognize what kind of person he is on his own, and identify what it is that he wants out of a relationship.

He wants second dates.
You want him to have second dates.

Why is he resisting your support?

Until you address whatever is going on in your friendship and your communication, he’s not going to hear you. If I were you, I’d get curious about that.

I would tell him one thing is more important than anything else: Be honest; Be yourself. You don’t want second dates anyway under false pretenses.

I am speaking from years of marriage under false pretenses…it is not all that.

Wait for the person that can accept the person you really are. I would say that the ‘no more second’ dates could be a sign that he is being who he really is. A good sign!