Pepper nods, as she has some idea of how hard that can be for a person not used to actual relationships. Not that she really knows much about Natasha's romantic history, but given how hard of a time the woman has opening up, she's willing to guess.

"Well, let me know if I can help, even by listening." Although Pepper knows better than to think it will be as simple as Natasha coming to her with a problem. "Now that I know to ask, you can expect well-intentioned prying on a regular basis."