It’s a really s--tty feeling, especially when it’s coming from someone they had thought of as a friend. While there’s no hard and fast timeline for when someone will be ready to date again, the closer they are to the break-up, the less likely they are to appreciate being asked out on a date. However, they are the ultimate arbiters of whether they’re ready to date again or not… and they may well discover that they aren’t. Third: if they are ready to date and you’re pretty sure you’re picking up mutual interest, invite the “no”. If you ask them out on a date, make it clear in advance that you’re cool if they aren’t feeling it.