1. Lets have a coffee, or I know this place where they make the best fries!
2. This movie has finally come out and I am dying to watch it. Wanna go with me at the cinema?
3. There's this party this weekend, wanna come?
I wouldn't, I'm too shy. With many failings and insecurities!
What I'm often interested in is usually too beautiful and either can & does take pickings from higher up the pecking order, has baggage and complications or just isn't / doesn't look interested!
I know this might seem a bit novel, but -- ask directly . Then the second part is to mentally prepare yourself to either answer, and try to detach from the outcome so you're not too nervous to ask in the first place. In other words, figure out ahead of time how you'll be okay regardless of how this person answers.
So without further ado -- the asking part itself. It does depend a lot on the individual person. I will admit that I'm kind of weird and out there, but I have yet to be turned down when I asked someone out. My invitation has ranged everywhere from a very blunt, "You smell nice. Want to go to the movies?" To, "Oh, you like ice skating? I used to figure skate, and the rink is open. Let's go, I'll pay for your rental." (apparently this directness is a little less weird in cities, but I'm a small-town girl and people are NOT used to it )
I have gotten some really weird looks in the past, but hey, I certainly stuck out in their minds. I think the biggest reason I haven't been turned down is because I'm upfront, matter-of-fact and relaxed about it. There's no nervousness or emotional charge -- I don't feel pressured, so neither do they. I didn't end up dating all of these guys, but I did end up with some awesome friendships that are still intact today. Asking out is about getting to know someone better, so the delivery is just the same as, "Hey, you're cool, let's go for a chat." After that, if you continue to be honest every step of the way, most other people will too. It's kind of scary sometimes, especially if you really don't want to creep them out, but it pays off and really tells you whether this other person is good to be around or not.
I'm pretty shy but I would ask if they wanted to grab a cup of coffee and if they agreed, we could relax and chat over coffee, then I might ask if they would be interested in having dinner with me.
Although to be honest, I'm pretty old fashioned and I would prefer to be asked rather than doing the asking.
When I was single I never asked complete strangers out.
Generally speaking there would be multiple interactions prior to going out whether it be casual conversations in person, over the phone, or via email. Based upon how those conversations went I would simply (ask) them out for a specific event that's taking place or the typical first date type of stuff (dinner, brunch, beach, dancing...etc)
Having conversations and building rapport ahead of time reduces the odds of having "bad first dates". The biggest challenge for people under these circumstances was working up the nerve to ask to exchange contact information. However today we live in a "social media" climate and people will give out their cell phone numbers, email addresses, and Facebook pages in a heartbeat. If someone refuses to exchange contact information that is a clear sign they're not interested in you romantically. Nothing ventured, nothing gained.
"If it's not worth asking for then it's not worth having."
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