I think I would love Barclay as a friend, but I don't feel he would work well for me as a romantic partner. I believe he would be too emotionally needy, which might have been ok for me in the past, but not now. If we got close, I imagine we could have fun sharing holodeck adventures (I would totally use it for exploring wild fantasies).
I did a cursory analysis of The Next Generation episodes, and I do believe that after the first season, Captain Picard had more romantic episodes than Commander Riker. I think however that Will's were much more casual flings and he had a more relaxed romantic attitude, which might give the impression that he had more relationships. Most of Captain Picard's were stronger romances. I am also counting actually any situation where the character was pursued by someone, or was treated as a sex symbol (for example, "Devil's Due" counts for Picard, and "True Q" counts for Riker).
I did a cursory analysis of The Next Generation episodes, and I do believe that after the first season, Captain Picard had more romantic episodes than Commander Riker. I think however that Will's were much more casual flings and he had a more relaxed romantic attitude, which might give the impression that he had more relationships. Most of Captain Picard's were stronger romances. I am also counting actually any situation where the character was pursued by someone, or was treated as a sex symbol (for example, "Devil's Due" counts for Picard, and "True Q" counts for Riker).