How to Text or Message Her for the First Time

Q: Okay, so I haven’t been online dating that long, but I’m getting frustrated already. I send out a ton of messages to older women, cause that’s my thing, but I hardly ever get a response. I’ve tried writing different kinds of messages: a joke, a poem, a hi… how was your day? but nothing. I think I’m average looking, and I had a female friend help write my profile, so I think it’s pretty good, but I can’t have her write my messages, or can I?

Oh, and I always have my IM (instant messaging) turned on, if they want to talk in real time, but no one has done that with me yet. Help! What am I doing wrong? Is there any kind of perfect message women are sure to respond to?
-Roy in Sheffield

A: Hi, Roy. You’re not alone. Don’t let the lack of responses deter you from using online dating to meet mature women. It’s really the best way. You may just need to refine your skills a little. I’m sure your profile is good; I always suggest asking a friend to help write it and/or proofread to make it shine. But no, you definitely can’t ask your friend to write your messages. The women who WILL meet you don’t want to get the surprise of, “Hmmm… you seem/sound so different online?!?”

Think about a first message in three components: length, content, and mood.

Length – “Hey, how are you?” isn’t going to cut it. Keep the casual tone, but aim for three to four sentences.

Content – Jokes and poems are too cheesy to throw a stranger’s way. If you’re funny and romantic that should come across in your profile. Focus on making a connection. She’ll like that you’ve picked up on details in her profile and that you share something in common.

Mood – Don’t go all “hot to trot” in a first message or ask a question you would only ask a close friend. Keep it light and friendly.

There is no perfect message as all women are individuals – what might attract one woman may turn another off. I do like your idea of sending out lots of first messages though; it’slike fishing (you’re dropping many lines in the water, waiting to see what bites.)

And only a small percentage of women use IM, so don’t use that as a barometer for how many women are interested.

Best of luck, Roy.

And when you do get responses, read: 10 Steps to a Great First Date

Cubs: Any tricks of the trade you can share for writing first online dating messages?

Who Should Message First?

Q: Dear Ava. I’ve been online dating for a few weeks, just finding my way around a few sites but haven’t done anything yet besides create my profile. I still need a few more pictures, and then I think I’ll be ready to start looking seriously. I did put in my profile that I prefer older women and adjusted my search to only show women at least five years older. Since I haven’t had any messages come through yet, I was wondering if many women message at all or if most wait to respond to what comes through to them. I was hoping I wouldn’t have to do all the work. lol. I guess I thought that older women would be more forward to going after men online because they’re like that in real life, at least from my experience. What do you think about this? – David

A: Hi David. I always tell online dating newbies not to rush when creating a profile. It’s all you’ve got to represent yourself and it needs to be good to stand out from the hundreds of others that come up in a woman’s search. So tweak away and have a close friend proofread or offer tips on how to make your best qualities shine through.

I’d like to have stats on the ratio of men-to-women first messages, but I’m going to say I do think men take the initiative more, a lot more. And I think this because of my own experience and that of both seasoned online daters I talk to . I think it’s natural for men to pursue women, and I think the majority of women like that, even us older ladies. A woman likes to know immediately that you’re interested and a first message indicates this. Of course some women, like myself, send messages occasionally, and some men like a take-charge kind of woman. It’s just more likely that you’ll get the dating ball rolling if you start sending.

So, get messaging. I recommend really scanning profiles, looking for your red flags (little things that turn you off) and making a list of your favorites. Send well-crafted first messages that are individually curtailed to each woman. No cut-and-paste! I still can’t believe men do this. Be ready for the low-ratio response rate. You have to know that women don’t respond to a man whose profile doesn’t interest her. Few women write back to say, “Sorry, but I just don’t think…” If you don’t have a tough skin, it will be hard at first, but online dating is so much better than hoping to bump into your next hookup or relationship.

Best of luck, David, in your new online pursuits!

Men: Do you think men should message first? Any messaging tips you can share?

How to Write a Great First Message

Are you contacting lots of older women online, yet receiving few responses. Your first contact is key in getting our attention. Sadly, it can often be something very minute that turns me off and on to reading the next possible match. Here are my tips on how to write a first message that will grab and hold a cougar’s attention:

Don’t Stress
You’ve already spent time (I hope) writing the best profile you can and have now found a woman that has you interested. Send a message! You have nothing to lose and the worst thing that will happen is no response.

Read her Profile
You may just see a hot photo and want to respond right away, but please guys, read her entire profile. Learning about her interests and personality will give you clues as to what to say in that first message. Her knowing you took the time gives you instant bonus points.

I don’t mean as basic as “Hey, how’s it going?”, but you simply want to introduce yourself and make a connection. If you can find a common interest you share, mention it and expand a little on your own experience. No multiple paragraph messages please, but no one-liners either. I’m a sucker for a little humour and quirkiness. Online dating should be fun and adventurous.

This means no clichéd pick-up lines or long-winded poems. I can’t believe guys think these will work, but I still get them and send them straight to the trash bin. Older women want a guy who sounds real and confident enough not to resort to cheesy refrains.

Park the Ego
You don’t need to impress a woman in your first message. There will be plenty of time for that later. You merely want to grab her attention and have her wondering more about you, which will get her checking out your profile.

Be Confident
This is even possible for shy people. Online dating helps get the ball rolling without the nervousness of face-to-face interactions. And if things don’t pan out, you are able to retreat just as easily.

Follow her Lead
If she does respond to your message, follow her lead. If she asks you questions, answer, and ask her a couple more. She may want to get to know you better before meeting. Don’t be pushy because older women do know what they want and when they want it.

Do not become discouraged when a woman you’ve been dying to message and hopefully meet doesn’t respond – this is par for the online course. Drop a few more lines and see what bites.

Hope this advice helps you with that all important first message. Any tips you can share?

First Messages That Won’t Get a Reply

I’ve recently returned to online dating after a breakup. After receiving many messages that are cringe-worthy or just a straight-up turn off, I was inspired to write about it. I’m going to share some of these messages and tell you exactly why they fell flat for me. Some may be obvious while others may seem fine, but nonetheless were irksome. I hope by sharing my thoughts, I will help you from making similar mistakes.

Bad First Messages

“How are you today”
I get a lot of “hi” and “how’s it goin’?” type of messages… snorefest! Lazy lazy lazy. Did you just see my picture and quickly send this message. If you don’t have time to read my profile and personalize a message, I’m not interested. Most of these go straight to the trash.

“If I get your body I never sleep”
Gross! Really? If you think this is going to get my attention, you’re right… just not the kind of attention you’re hoping for. It’s crass and presumptuous. Also, the writing sounds like a robot. I hope he didn’t send this to anyone else!

“You’re so intriguing. Those eyes cannot conceal your playful ways. I have revealed your inner secrets with just one glance.”
It’s not the worst message I’ve received, but it creeped me out a little. I’m sure this guy thought he was being attentive or something, but it’s just too stalker-like for me to trust. This message tries too hard, and in the process fails.

“Can we explore a companionship?”
This message is too short and doesn’t really say anything. I want to know that a man read my profile and found something specific about me that appealed to him. If you are new to online dating, ask a friend with some experience to help you out.

“Text me and I will send pics… interested in an hour *** 877 ****”
A message from a man without profile pics… and he hadn’t filled out any sections in his profile!!! You have to be seriously delusional to think a woman is going to text a stranger (thus giving him her phone number!) and want to meet him immediately before knowing a single thing about him. Get real!!!

“Hey. How is it going. I am alone with no one to love to chill to party to flirt. i am alone in life with no one to share my heart with. Then i came across your beautiful face and i want to see that face smiling at me so will you join my life for those lovely moments. Hope to hear back”
This has that robot-speak I mentioned earlier, not to mention horrible grammar. This guy was trying to be sentimental (with a stranger!), and it just comes off as desperate and cheesy. Wait until you start dating someone before you get romantic, please.

And one message I didn’t include was as long as the his profile. These novella-length messages are off-putting because they reek of desperation. I don’t want to feel strong-armed into dating someone. A few sentences should be enough to catch a woman’s attention.

I hope these examples will help you to avoid writing a message that gets ignored.

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