Emailing is the digital equivalent of courtship. Stand out. Take a chance. If you don’t, you risk sounding like everybody else. And in a fast and busy medium like online dating, sounding like everybody else is about the worst thing you can possibly do.
Keep it short and sweet
Keep your introductory message to 5 - 7 sentences at the most. Too short in a first contact email will make her think you’re sending off dozens of messages (and she’s not that special for receiving one!) Go too long and you risk losing her interest.
Start with a unique subject line
Starting with hey, hi, hi there, or how are you? are all perfectly fine and polite, however think about starting with something unique that stands out to hook her interest. In fact, an OKCupid survey found it is smarter to use no traditional salutation at all and just dive into whatever you have to say such as "Wow! I never thought I’d find someone who loves archery as much as I do!“ Just think about what a typical woman’s inbox looks like:
Subject: (No subject)
Subject: What’s up
Subject: (No Subject)
Subject: (No Subject)
Subject: Battle of the Lasagnas…
Subject: You are beautiful…
Which one of the above examples stands out from the crowd and makes you want to open it? And if you think the last example (you are beautiful) will work, please learn the fundamentals of attraction immediately because you are unintentionally killing yourself! Battle of the Lasagnas stands out from the competition because it generates interest and creates curiosity and ultimately is an eye-catching email subject line.
Be personal and positive
The goal here is try and stand out from everyone else in the building. Keep 'the vibe' upbeat and personal and try to establish a connection with her. Talk about one of her hobbies, the book she just read, how cute her dog is… anything that shows you've read her profile. Use phrases such as I'm curious what... noticed that...you mentioned.... Also, don’t rehash your profile; she can already see that you’re a 32-year-old man from Caulfield who enjoys fishing on the weekend. Essentially, focus on the person and why they should write to you.
Relate, then add
Ideally, you should stick to one topic so your message is focused. If there are two that go hand-in-hand, you can expand, but more than that and you risk sounding too interested for a simple hello. Relate well to her and show interest by asking questions, but also add enough detail about your own life to keep the momentum moving. Avoid talking about religion, politics, past relationships, marriage and heavier topics such as personal health issues (she doesn't need to know you had a bowel obstruction operation last week!) and try to keep topics of work and your children (if you have any) to a minimum. It doesn't hurt to even start a fun, friendly debate which starts a dialogue between you such as "You say you love your iPod and the sand, so remind me never to lend you my iPod before you wreck it at the beach!". The focus of your initial email conversation should be about the two of you, to allow you get to know each other and hopefully develop a rapport.
To figure out if your email is coming across as genuine, try reading it out loud. If it sounds conversational—like something you’d actually say face to face—then you’re on the right track. Of course, a well-placed witty line or one-liner can be really effective, but if it doesn't come naturally to you it's much better projecting warmth than coming off as sarcastic or that you are trying too hard. Humour is very subjective – what’s funny to you may be incomprehensible to your potential date. Never forget you are in essence writing to a stranger who may not yet appreciate your rapier wit.
Ask her a question
Your profile writeup 'call to action' may be subtle, however emails should be more direct. Ask a question about her (based on what you’ve read in her profile) and where her response can’t be limited to Yes or No. The easier you can make it for the recipient to respond, the more likely you are to get a reply. Only ask one question and keep it simple. Asking three questions for example can become overwhelming or feel like badgering, and she may not respond at all. If you can find a similarity between you - call it out and then weave it into your question to her. For example “You’ve said you want to travel to Rome. That’s one place I’ve never been – what places are on your hit list?” If there isn't much detail in her profile and you're grasping at straws for a connection, make a joke of it even. If she says she’s looking for someone kind and smart, you could say something like “I’m kind of smart. Is that close enough?” You obviously don't have to be laugh-out-loud funny, but it does need to be an original take on the material you’re given to work with.
Bad grammar and bad spelling are distracting and are huge turn-offs so make sure you spell check your emails. Netspeak such as ur, u, wat, wont, r, u, ya, cant, hit, realy, luv, wat etc also make a terrible first impression. The only exception are expressions of amusement such as haha and lol, however hehe not so much because it’s a little evil sounding. People like a sense of humour, and you need to be casual to convey genuine laughter.
Use emoticons sparingly
In a male-female situation (and particularly from the guys perspective) use emoticons sparingly as they can give off energy that isn’t confident. Use once in an email and not in every email as any more is distracting. For example, save your smiley face to the email when you eventually ask her out. This is when you want to convey more genuine emotion and excitement. And stick with the plain smiley faces … even just the symbol :) …rather than the variations.
Write with confidence
People like confidence, far more than wishy-washy use of language. What kind of person would you rather hang out with: a person who comes off as independent and strong or someone who'd give their right arm to be with you before you’ve even met?
- Writing things like, “you probably won’t answer this but ..” or “I can’t believe I’m doing this but .." makes you look unsure of yourself and it’s not going to get the women flocking to your profile.
- If you are outside her criteria, call it out (which shows you have read her profile) but then put a positive spin on why you think you’d be a good match. For example, if her maximum age range is 42yrs and you’re 45yrs you could write “I realise I’m just outside of your ideal age range, but I feel we have a lot of in common and…" OR put a funny spin on it such as “I thought of being 5’11” just for you...but I figured that if honesty got me this far, why blow it now? I’m 6’1” in 3” heels so does that cut it?”
End With Your Name
Signing with your name instantly warms up the tone of the email. While this may sound obvious, some guys leave it off and risk coming across as mysterious - and not in a good way. Needles to say, you should also skip any extraneous information, like a full signature with your title, email address and phone number.
Attract Quality not Quantity
Unless you're seeking a casual no-strings-attached relationship, guys who put up a front, who are cocky, who try too hard, or push the envelope with sex talk won't impress "quality" women because she knows these acts are transparent. If you approached a gorgeous girl in real life with these tactics, it would either result in an eye roll or attract a lower-quality mate, and the same is true in the virtual dating world.
- Template emails are the pickup lines of the web. Being proactive and sending an appropriate number of emails is important, but avoid templates messages that are so generic it's obvious they are copy-and-paste jobs. It's fine to create a message outline, however be sure to erase signs of it being generic, by getting specific.
- A little email flirtation is never a bad thing, but you don't want your message to scream "you're not worth getting to know more, so let's just meet offline and be inappropriate together" so skip sexual content and physical compliments such as "I think you're ...hot ...sexy ....gorgeous".
- Leaving your number in your first email message is the equivalent of saying I don’t want to put much effort into this, but I figure if I write to enough people, maybe someone will respond. “Why don’t you give me a call when you get a chance” is not an open-ended question because (for any self-respecting woman) the answer is already No. It's impersonal and shows that you are more of a ‘player’ than the real deal.
Honesty, depth and creativity are the keys to the initial email exchange. So guys aim high! Choose wisely and take the time to make each girl feel special in your first email message.