[JA7]

Hi April,

I have been family friends with this girl and would love to take the chance and move the conversation (below) from friends chatting to going on a date.

How should I proceed?

Me – 9/30, 7:27pm – bday was great and getting old is not so bad! Let me know about next week wink emoticon

Her – 9/30, 2:33pm – Haha hope you had a good birthday! This week is too tough but we can try for next week. I’ll let you know, hope you had a good birthday!

Me – 9/29, 1:19pm – Thanks! I mean one happy was nice but double happy birthday….pretty freaking awesome of you smile emoticon lol I’m working for a contractor/developer in Beverly Hills, where are you now? Free to meet for a drink later this week?

Her – 9/29, 10:49am – Happy happy birthday!! Would love to catch up! Where are you now working?

Me – 9/27, 11:49am – Hey, things are good. Started a new job about a month ago and I’m enjoying learning a lot of new things. And my birthday is coming up next week so I’m excited to celebrate that. What’s new in your life? I feel we haven’t talked in ages. We need to catch up.

Her – 9/27, 1:16am – Things are good, busy! What are you doing now?

Me – 9/26, 9:52pm – Gmar chatima tova to you and the family! I’m doing really great. How are things with you?

Her – 9/26, 9:23pm – Shanah tovah!! How are you?

Me – 9/26, 7:48 pm – Hey, great seeing you and the fam at Yom Kippur! Sorry didn’t have a chance to come and say hi, but hope all is well

[April Masini, your AskApril]

Pick up the phone and ask her out on a date. 🙂 Women love to hear the sound of a man’s voice — it’s a very seductive tool that doesn’t come through when you’re using text and e-mail. Also, taking the conversation out of text, which is pretty casual, and onto the phone, signifies a change in the status of things. Make it clear that this is a date, when you do call, and let her know you like her — flirt and compliment her, so she knows you’re into her, not just in the neighborhood with a free night with no plans. 😉

Let me know how things go — and if you have any other questions, let me know!

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[Natalie Noah]

The dynamic here is warm, friendly, and clearly comfortable but it’s also stuck in that “friendly, familiar, safe” lane. Texting created momentum, but not direction. What she responded with (“this week is tough, maybe next week”) isn’t a rejection it’s neutral. She didn’t shut you down, she didn’t avoid the idea of meeting, but she also didn’t lean in. When things sit in that middle space, the best way to shift the energy is to change the medium. Text keeps things soft and noncommittal. A call creates clarity, confidence, and chemistry.

A direct phone call also shows intent something text can’t fully communicate. Instead of floating casual suggestions, make it unmistakably clear that you’re asking her on a real date, not just a catch-up between old family friends. A warm tone, a little flirtation, and a straightforward invitation (“I’d love to take you out how’s Thursday evening?”) does two things at once: it signals interest and also gives her something real to respond to. Most women appreciate that kind of grounded confidence.

And if she says yes, the tone of the relationship shifts instantly. If she hesitates or keeps things vague, that’s valuable clarity too but you won’t know until you take it out of text and into a real conversation. The opportunity is there. You just need to steer it.

[Aida Omar]

If you like her, be bold and direct.
Don’t text her. Call her and ask her for a date. If she says yes, take her out on a date and tell her clearly how much you like her so that she doesn’t think of you as just a family friend.

[Carl Matthew]

Instead of texting, why don’t you call her? Women usually prefer that because they can feel the conversation more, it becomes more personal and romantic. It kind of levels up the interaction when it’s a phone call.
Ask her out on a date so you can get to know her better. Also, admit that you like her in a more romantic way. Show her clearly that you’re interested.
Compliment her on different things, like how beautiful she is and also her personality. Then just see how things turn out from there.

[Member]

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