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Alright peeps I need some tips on how to ask someone out. for some reason I have no idea why this is so terrifying to me asking this woman out maybe because I'm scared of rejection how do I summon a courage to do this?.

Hey! I'm not a very experienced dater, as I ended up falling for the first guy I went on more than 3 dates with post-divorce, but I just wanted to ask - how do you know this woman? If it's from a dating app or website, I think that pretty much smooths the way since the expectation is that she's here for it, as the kids say. If you know her in some non-looking-for-dates way then it's a bit trickier. Especially if you work together.

I will tell you that I met my bf after a slew of lackluster first dates and a slight heartbreak from the first guy that I really fell for - long story - but a lot of guys are kind of wishy-washy and indirect. BF had asked me out and when I said yes, he told me that he was glad I said yes, he always felt like a teenager when he was asking a woman out. I found that bit of honesty endearing. But he was direct when he asked me out. And after our first date, he said, "I had a really nice time with you, and I'd like to take you out again sometime if you'd like." And again, I was very impressed with his direct, honest approach and complete lack of game-playing. By contrast, a friend of mine had been chatting with a guy she met on bumble for a while, and he was circumspectly trying to feel her out about a date - she said, "Are you asking me out?" and his reply was, "I'm not NOT asking you out." So that became a running joke. It's much more attractive to take the risk, put yourself out there, and be direct about your intentions than the "not not asking you out" kinda deal.

Try not to attach yourself too much the outcome. Easier said than done, I know, but you are fearful because you are attached to the outcome and somewhere in your psyche you believe that a rejection would be a reflection on you and your worth.

It’s a bit like getting over stage fright before a speech by picturing everyone in the audience sitting in their underwear. While it’s a bit silly in terms of actual advice, the point is there’s nothing better about the audience waiting to hear you speak than you yourself. You’re all just a bunch of finite, fairly confused sentient humans trying to figure out the world before your 8th or 9th decade takes you out of the running.

So asking this woman out on a date is not a special event. Truly, it is not. It is not an important event, believe it or not. You are asking out someone you have an attraction to and an affinity for to go on a date.

Big deal.

There is nothing special about this particular woman, either.

I don’t say that in a harsh way or to be dismissive of her. I only say that to help see that she is among thousands, probably tens of thousands, of women you might be uniquely compatible with — and a great many of them live in your own backyard. In other words the saying “plenty of fish in the sea” is true both for real fishermen and for men like you looking for a date.

There are any number of reasons she could say no that have nothing to do with you at all or that only have to do with her own self-worth or insecurities — or she could simply say no because she doesn’t want to or isn’t attracted to you. Or she’s having a bad day. Or she feels bloated and unattractive. Who knows? Who cares?

In which case why would you want her to say yes? See how that works? The only way you would possibly want her to say yes is because she’s actually interested in you, attracted to you and excited by the prospect of spending some time with you.

However, many women are simply waiting for a particular man or men to ask them out. I’m sure I’ll get in some trouble for saying this, but most women appreciate a man who takes the initiative and has enough self confidence to ask them out. Also consider that women are approached and asked for dates ALL THE TIME. If they are reasonably attractive, they are surrounded by male attention. And? So what!

If she says no, she’s doing you a favor. Think about it. She wasn’t in a place for whatever reason to be available for you. If she says no, you’re standing exactly where you were 10-20 seconds before you asked her, which is: she’s not going on a date with you. Materially you are completely unaffected and you haven’t wasted money on a date that wasn’t going to work out. Emotionally, you should also be unaffected because she wasn’t doing anything but saying no to a straightforward question you asked.

And now because she didn’t waste your time, you can simply move on to the next woman. Because there are many other women in your geographic proximity who are compatible with you and who would be attracted to you if you knew them — and vice versa.

Adopt a mentality of abundance about women rather than scarcity. The more you attach too much unwarranted significance to one, the more you are buying into a false mentality of scarcity.

Read The Way of the Superior Man and begin focusing on your mission in life.

I agree with JanaGreen that the direct and honest approach is the best way. Games are for children. Direct and honest will also boost your self confidence in approaching her because you won’t be worrying about adopting some sort of “script” that is artificial to you.

Put your shoulders back, head up, lower your voice an octave and ask her directly and firmly without hesitation. Your life does not depend on this.

The date itself should also be uncomplicated and simple and direct.

“Can I take you out for a drink? I was thinking tomorrow at 5 pm at _____.”

If she says no, you say “Ok, it was nice talking to you, have a great week.”

And then move on to the next available prospect. Do not waste any more time asking her again, approaching her next week or next month.

Just move on. Because I guarantee that soon another woman will say yes.

[This message edited by Thumos at 12:02 AM, July 28th (Tuesday)]

I also agree that being direct is the best approach, albeit tricky right now with CV19. So make sure that area of comfort is covered.

If it is from online, I really do not want to message more than a week. Originally I put that information out fairly early on and it seemed to scare men off IMMEDIATELY or else they thought I was a Russian call girl or something??? So I stopped.

Now if a man does not ask to at least talk or meet within a week(ish)+...I will back off and time my responses to his. If 3-4 days lapse with no return communication, I will unmatch.

I’m patient, but CV19 has myself and a lot of people doing things differently.

sorry for the late reply, thanks for all the info I appreciated it if I see her again at my work i'll just straight up ask her if she want's to grab coffee and go from there. hopefully I won't stutter asking her out lol

Good luck somejaykid!!! I hope it goes well.

If it is from online, I really do not want to message more than a week.

Oh yes! Same! I initially wasted so much time messaging with guys before we met up. I talked with this one guy for weeks and thought I was really into him. Met up and just zero sparks. I really didn't think I'd like BF but ended up really liking him in person much better than over text. I think it's impossible to tell until you're face to face.

It's easy for us to be keyboard warriors giving advice. Best of luck. Just try to be yourself and not someone else. And don't take it hard or personally if she says no. If, for example, she has a boyfriend and says no, then you'll know what a great character she has!

As others have stated, the direct way is the way to go about this. Live life without regrets! I know those post-divorce connections can be daunting, but you only live once. And if it doesn't get off the ground or work out in the long run, at least you tried, and that's a very useful tool to keep in your belt.