It is often said, that:

  1. The worst she can say is NO.

  2. Keep trying, there are many women. Someone would like you back.

  3. Don't use online dating, find someone in your offline circles.

---

While all these advises seem legit on their own, when combined they create a tricky situation.

Man tried his chances with Amanda and got rejected. She gossiped about it with Betty, Charlotte and Diana.

Now when he tries to approach any other girl in the same circle, she knows that he was previously rejected by her friend. This drastically reduces chances and gives him bad reputation. He will be considered creep and desperate even if he approaches politely and takes rejection gracefully.

This was pointed out here before, but many women objected. Maybe it is just OP's insinuation and real women don't care if man was already rejected before by some of their common friends?

So there was a recent post at ask women no censor: https://np.reddit.com/r/AskWomenNoCensor/comments/1stf73n/how_do_you_feel_about_dating_a_man_who_previously/

It was exactly about such situation: approaching someone who knows you were rejected by her friend. I'll quote some the answers:

> To answer your question, generally women do not like it when you ask them out after very recently pursuing someone they know. It reads as desperate.

> I mean... in theory it doesn't preclude you doing that, but you're going to start getting a reputation for being that guy at work who just tries to date all his female coworkers if he thinks there's any chance they'd bang him. Generally keep dating and work separate, but if you do get together with someone it's a lot less weird if it's a situation where you gradually get to know them and realise you happen to have a good connection. My mum and dad worked in different departments at a large company and that's how they met and struck up a friendship and started dating eventually, but my dad hadn't been going around asking out multiple women till someone said yes. Doing that makes a guy seem desperate and not actually interested in a specific woman so much as he's interested in getting laid and/or assuaging loneliness.

> I mean, it would probably put me off. It gives me the ick and it comes across a bit desperate. But I'd tread very carefully, you don't want to make your colleagues uncomfortable. Ultimately, you're there to work not advance your love life.

> I mean, if you WANT to be an office joke go for it. But I can’t see how someone can start a new job and immediately begin asking multiple women out without turning themselves into an office joke.

> I'm with someone who previously asked out someone I know, but we started dating more than six months after that happened, and after we organically got closer and developed feelings for each other. In your situation it may seem like you're just going from one woman to the next, asking out whoever is available and seeing what sticks. Even if that's not your intention, it will likely come off that way. If you happen to get closer to one of these women over time and then ask her out, that should be fine (if we ignore every other potential problem that comes with dating your coworkers lol).

---

So basically asking out women in your offline circles is not a solution. You can try. Chances are you will fail and will be rejected. And her "NO" has consequences - effectively all the women in the same circle said "NO".

There answers like "you have to slowly organically get to know each other" but in the end it means, "before you drop plausible deniability make sure she really likes you because consequences of a failure are very significant."

OLD are screwed, but offline attempts are either cold approaching which is creepy, or trying chances within circle - but you only have one attempt.