He folds his arm over her shoulder, giving her a gentle pat of reassurance. "Other people do tend to be a risky gamble," of that he is sure. He's not been personally in the dating game for... a very long time now, but it's a lesson you only need to learn once. "But, if I may be so cliche as to quote a Romantic, sometimes it's better to have loved and lost, than never to have loved at all."
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It's a cliche for a reason, after all.