Online Dating Guide & Blog

For this discussion email refers to whatever method the service you are using allows you to write a message to another member. This discussion is primarily for sites such as Match.com where you will need to begin the communication on your own. This advice may still be helpful for sites such as eHarmony or MatchAffinity, however these services guide the communication far more.

Writing a first email is the area where I made the biggest mistakes for the longest period of time when dating online. I would write overly long and, in my head, witty emails that very rarely received responses. Once, I wrote no less than two pages based on a girl’s heading to her profile. The HEADING! I thought I was making conversation but all I was making was a girl scared. I really did mean well. I just didn’t know what I was doing.

Writing a Better First Email

My rule here is very simple: keep your first email very short. Give anything longer than three sentences a good, hard look before sending. There are several reasons I’m for short first emails.

• Your profile is what you use to sell yourself, not your first email. While I feel that your profile should be a constant battle between brevity and substance, it should definitely hold enough for someone to make a decision about communicating with you. If it doesn’t, don’t try and fix it in your emails: go back to your profile and improve that first. The email should be the bait to get someone to view your profile.
• If they don’t like your profile, long-winded emails are wasting your time.
• You have to keep your weird factor low. Never forget that you are battling the bad impressions created by every weird person who has come before you.
• For reasons beyond my comprehension, short emails can come off as confident. Worded wrongly they can come off as cocky but even that is more acceptable than psycho.

Okay…So What Should I Include?

So what do you include in this short introductory email? Here’s my short 3-point list:

1. First, try to include something to prove you read their profile. Many guys out there spam the same email to every girl they find attractive; most girls catch on to this and then look for it in other emails. Obviously, women can be initiating emails too, so this rule applies to them as well…but I’ve never heard of women who spam like this.

2. Second, if you find something in a profile that you have in common or there is something you like about the profile, mention that area (if there are multiple things you really like, just mention one).
3. Finally, I’d recommend that you ask a question. Often this can be about the common interest you mention but any question is better than none. If you can’t think of any questions, why not ask them out on a date? As I’ve discussed in my thoughts on the first date, better to ask too soon than waiting too long.

Exaggerating Your Thoughts on Shared Interests

One optional approach to emailing that I took is if I had something slightly in common with the profile I was reading, I would express more excitement about the similarity than truly existed. I wouldn’t flat-out lie but I would make a bigger deal of things than was true.

For example, I enjoy an occasional day walking around a big city. If someone mentioned this in her profile I wouldn’t say “I like going to big cities, too.” I would say “I love walking through the city too…although some days I think I must be the only one!”. Saying that I love walking through the city is a stretch but I would want to add some strength to my statement.

Most emotion is lost in online communication (and anyone who has used a :) in emails agrees with me). To avoid this, I would try to show my true level of interest by exaggerating it. Also, I felt that making someone feel “liked” early on would help them feel more comfortable and more likely to respond.

Sample Emails

Let’s look at a few real profiles, albeit very short ones, and I’ll write a first email that I would send if I were interested in meeting the girl. The first profile is what I would consider a “normal” email where contact is made but not much else. The next two are special cases where asking the girl out occurs in the first email. In my online dating life, it was uncommon for me to ask a girl out in the first email but I felt that in both the second and third example, it was the best option based off of the profile.

I’ll be changing some profile text to avoid intruding on someone’s life but will keep the general ideas expressed in these profiles the same.

Profile 1:

This young lady devoted half of her profile to talking, in some fashion, about being sociable. This seems like one of the better points of focus when writing the email:

Response 1:

My approach here is to be positive but brief. I make it clear I read her profile and that I’m interested in who she is. I don’t ask her out but the swing dancing reference is there to say “If you write back, I just might”. I chose swing dancing because I’ve done it a few times and by mentioning it I’m backing up the statement that I enjoy social activity. The goal here is to get her interest, have her look at my profile and if she likes what she sees, move forward.

Photo by Ed Yourdon

Now this is someone I would not likely contact but I’m trying to be fair by grabbing profiles at random, not just those I can write an email to easiest. She openly admits concern over stalkers (enough concern that she’s included no photo of herself) so not coming off as weird is very important. However, something about her profile makes me feel like she may not respond to many emails, perhaps due to her confidence in what she wants, so I’m more willing to take a risk. The important parts again are: don’t appear like a stalker and to be brief. In this case I’m going to play off her professed “likes” by attempting to be unique and creative when I write my email:

Reponse 2:

I’d title the email something like “Mirror, Mirror”. Would this work? Chances are no, but if it does she’s really going to enjoy it. Even in the case where she decides it is horribly corny, she might appreciate the unique quality it had. I still keep the email short and include information that proves I’ve actually read her profile. I also ask her out in the first email because:

• someone adventurous doesn’t want to email for long they want to meet people
• I’m asking before I’ve seen a picture which may improve my odds of not being stalker material.

Profile 3:

This is an example of how sometimes profiles are too short and give you no clues to who the person is. With this type of profile, I always felt like simply asking them out on safe date in the first email is fine. There’s not too much to work with here aside from asking travel questions which, by looking at her profile, probably already happens in every email she receives. In this case, I’d just flat out ask her out. I know this looks like nothing but I’ve had success with these types of emails (my wife being the best example):

Response 3:

For all these examples, I’ve intentionally chosen profiles that were very short to keep the examples to a reasonable size. Most profiles should have much more information for you to work with but the same ideas apply:

Also, regardless what any book or person tells you, better to listen to your gut and break any “rules” (such as keeping the email short) when you think it would work to your favor. For example, in the Profile 3, creating an invitation to have a drink that looked like a travel itinerary might work well if she had mentioned enjoying creativity or if her profile was very creative.

Everything else aside, just coming off normal and interested goes a long way.

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