Ask A Woman: The Hunt for Red Hot Date.
If you’ve got a question that needs the female treatment, chances are you’re not the only one who wants to ask it. Beth is our source for the answers. From opinions on men’s style to decoding the sometimes mysterious ways of women, she’ll take on a different question every Thursday. She also might provide an answer without waiting to be asked. That happens from time to time too. Click here to get to know Beth, then get in touch with her by sending your question to: email@example.com .
I volunteer on Saturdays tutoring middle school kids and there’s a fellow tutor that I’ve meant to ask out. She’s seems kind and funny. She’s extremely driven to do some crazy things I’d never attempt professionally, which I frankly admire. Yes, she’s cute as a button, too.
Our program runs over the school year and the last session was this past week – she wasn’t there. Of course, I’d meant to ask her out the week prior but I waited till this last week to ask her for her number – I’ve had ample opportunity as we’ve been coming down together on the train after the program.
Here’s where we are – the only way I can reach out to her is to ask the person who coordinates the program to pass her number to me or pass my number along to her. I wouldn’t want to put the person coordinating the program in an awkward position having to maybe pass on some private information that they don’t feel comfortable sharing so I’m thinking I just ask to have my number passed along. In fact, I think she’ll say yes (and I’m not the most optimistic person when it comes to these things) – I’m just not sure how to get to asking the question now. What do you think is the right way to go here?
Sometimes dudes write in about a dating issue and all they really need is someone to tell them they’re already doing the right thing. This would be you. You’re so close! You’re on the right track! Look at all these reasonable, upstanding men reading Dappered who have really thought through their decisions when it comes to pursuing women–you readers make me feel optimistic for all the single gals out there. Truly. It’s an honor to hear from all of you.
I feel where you’re coming from with the, “Damn, should’ve asked her for that number when I had the chance.” We’ve all been there–have you ever looked at the “Missed Connections” part of Craigslist? People regretting their inaction all over the place. But your idea to contact the program coordinator is a solid one. AND, your instinct that this person might feel uncomfortable releasing another volunteer’s phone number is also right on. So I’m just here to reassure you–yes, call or email the program coordinator and say, hey, thanks for your support this past school year, it was a great experience. Also…I was hoping to connect with so-and-so over the summer but I don’t have her phone number or email address, and she doesn’t have mine. Would you mind passing on my phone number to her or asking if she minds your giving me her phone number? Hopefully the program coordinator is a sympathetic person who will do a little extra leg work to help you out. If she doesn’t, consider other avenues to getting in touch with your lady–Facebook if you know her last name, other volunteers from the program who might know her, riding the same train you took with her day and night to see if she shows up on it (kidding about that last one).
“You ran over my dog….”
Once you get the contact information of this woman, keep it casual and upfront. “I had such a great time hanging out with you this school year, would you like to get a drink/meet for lunch/go for coffee/take a walk this weekend?” If she says yes, awesome–you’re on your way to having a summer romance. And if on the off chance you misread her and she’s not interested, don’t take it too hard. “Okay, well, it was good chatting and maybe I’ll see you next school year.” Be light and get off the phone as soon as possible. The hardest part about dating, initially, is always this–putting yourself out there. I sound like a broken record, I know, but you just have to do it. Take a chance, be willing to be vulnerable, be willing to experience pain and disappointment (because this comes hand-in-hand with joy and satisfaction). Life’s richness is borne of equal parts success and rejection.
Good luck TK. Anyone else out there embarking on a summer romance?
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