The regular icons mean those sims are participating in a group outing. The hearts mean the outing is a date.
What exactly makes those happen sometimes and not other times I've never been able to figure out. If Sam asks Sue to come over, sometimes it's an outing, even if it's just at Sam's house, sometimes not. Sometimes it's not even an outing if Sam asks Sue to go somewhere. Sometimes a "date" starts with just a romantic interaction, even if neither Sam or Sue asked the other out. You can always end the outing/date by selecting one of the sims and choosing Disband Group (for outings) and End Date (for dates, obviously.) It might cost you a little of the relationship, however, if the group or couple hasn't had much fun yet on their "outing."