Dating Emails Questions Extravaganza

December 16, 2020 by Andrew Small No Comments

The Anon-O-Box has been way more popular than we ever thought it would be! (This is great, so keep the questions flowing!)

We are planning on doing an all Anon-O-Box week coming up soon, so if your question hasn’t been answered, we’re hoping to clean out the box and get ‘em all done!

Today’s Anon-O-Box is going to answer a bunch of questions regarding everyone’s favorite topic – dating site emails! How to write them, what not to write, how to reply in a way that doesn’t scare away people…

Here goes!

Emailing Someone With A Short Profile

Dear Anon-O-Box,

Several times I’ve found profiles with only a few lines and a picture. I’m attracted to the photo and get some sense that they’re nice, but there’s nothing to write about in terms of their interests.

– Blood from a Stone

Dear Blood,

All isn’t lost! In the case of new members, sometimes people want to get their account set up quickly and plan on coming back to fill in their profile. The good thing is that usually those areas of the profile where you tick off boxes about your interests are filled in.

If that’s the case, I’d find one of those to write about. For example, if you see the girl likes Hiking/Camping, you can write about your latest camping trip and ask her about her favorite outdoor adventure.

If there’s absolutely nothing checked off (or lots of “No Answer’s) there’s a chance that you’re looking at either a) a spammer or b) a really lazy person. You can try a generic introduction email about yourself and add a line about how you hope they’re as sweet as their smile (or some equally cheesy but non-threatening pickup line).

The Second Email – Do I Ask Her Out?

Dear Anon-O-Box,

Ok, so I sent her an email, and she’s responded, and I’ve sent one back, and her response is meh. How can I spruce things up or keep things going? Am I supposed to ask her out on the second email?

– Second Email Meh

Dear Second,

If her response is meh, it could be from a variety of things. It’s really hard for me to tell without seeing the exact email chain. You’ve left me to speculate, so that’s what I’ll do:

Your second email was way too long and you came on too strong.
Your second email mentioned something she didn’t like and she’s lost interest.
She’s being polite in replying, but either isn’t interested or someone else is occupying her interest.
She wanted to reply, but was really busy, so had to shoot something off quickly.

You can spruce things up and write her another email, bringing up some things that you know she’s interested in (reference her profile and previous emails). Ask her if she’ll be attending some local event that might interest her… but avoid asking her on the date this early. If she were receptive to being asked out, her second reply would have been more than just meh.

Dropped Off the Face of the Planet

Dear Anon-O-Box,

I am emailing with a person from an online dating site. She then stopped emailing with me. As far as I can tell I haven’t said anything that should scare her away. Should I send her a general “Hey what’s up” email or wait for her to email me back? If I send her an email when is the appropriate amount of time to wait before sending one?

-Waiting and Confused

Dear Waiting,

If it’s been a week or so, you can definitely send a follow-up email. There’s a chance something came up in her life, or she was semi-seriously dating someone and put you on the back burner. Don’t write your guesses as to the cause of her absence in your email, but write something short and sweet that says you hope she’s been doing well and that you’ve missed writing with her. Invite her to start up the conversation again.

If she doesn’t reply, though, be prepared to let her go.

One Sided Conversations: Getting Her to Ask Questions

Dear Anon-O-Box,

Once you get a girl to answer your first email, how do you get her to talk?

Of the women who respond to my initial emails, they only answer my questions, never ask any of their own. Even when I encourage them to ask some! I can only get a few sentences out of them and that’s it, regardless of how tailored-to-her I make my inquiries and comments. Why is she responding if she’s not going to talk?

-One Sided Talker

Dear One,

There are people who will respond to all emails just because they’re super polite, not necessarily that they’re interested. They are pretty few and far between, so let’s assume that if she replies and it’s not a “no thanks” that she’s at least somewhat interested.

If you find she’s been responsive and giving you answers to your questions, then you’re going to want to talk about something in your life that will make her want to ask you a question. It’s like asking her to ask you a question, but without actually going there.

For example:

“I notice that you love traveling. If you want, I’d love to tell you about my trip to Austria last summer. I have some beautiful pictures of the mountains and a pretty funny one with a mountain goat (but not like that!)“

If a dangling carrot like this doesn’t get her to bite, then you may want to try to move the conversation to IMs or phone, where you can have a more equal conversation.

She Writes Back… Once

Dear Anon-O-Box,

I have been surfing many dating sites trying to find the right geek girl for me. I have contacted and been contacted by a few different women, but the emails only last for 2 emails. It seems that no matter what I say in the second message I send, it’s the guillotine that kills that spark of interest.

I try to use the first message to ask the person of interest about themselves and to get a better understanding of who I’m talking to. I use the second message to try and get a better feel of who they are and allow them to know who I am. I usually try to allow much more of my personality to come through on message 2, while I try to keep message 1 much more formal. (Mostly so I don’t scare them away.)

What am I doing wrong that makes them run on the second strike.

Two Strikes

Dear Strikes,

As I mentioned to Second Email Meh above, there could be a lot going on that would cause her to run away after the second email. But I’m getting a feeling just from your letter that your second email is probably too long and involved… I could be wrong, so feel free to let me know. (I’m no psychic!)

I say this because you remind me of one of my real life friends who has been working on getting a girlfriend online for a while now. The kiss of death for him is always that he sends marathon emails as soon as a girl shows a tiny amount of interest in him.

Keep emails long enough to say something of value, but short enough to keep the recipient wanting to know more.

Happy dating, geek friends.

Useful Resources:

Changing from Jade Glasses to Rose-Colored

What Twitter Can Teach You About Dating Norwegian Men

Dealbreakers: How Much Do They Mean To You?

What Realtors Can Teach You About Online Dating

What Las Vegas Can Teach You About Online Dating

Reflecting the Season to Freshen Up Your Online Dating Profile

Online Dating Profile to Reality Translator

Why Do Girls Go For Jerks?

How to Find Dates in 3/4 Time!