I See Someone I Like – Now What?

So, you’ve signed up to a couple of dating sites and have actually found a few people you’d like to get to know better… maybe even date. What do you do now?

Well, you can put up your profile and wait for someone to contact you, but you’ll probably get much better results if you take the initiative. When you find someone interesting and feel the urge to say “Hey”, don’t be bashful! That person may just love to hear from you. After all, they created a profile, just like you, in hopes of meeting someone. You definitely won’t know unless you contact them and find out.

Ladies, don’t be shy – men love to be pursued!

How do you initiate contact?

The most common ways to contact someone is with an email, an instant message, or a ‘wink’.

I recommend saving the instant messaging until you’ve exchanged a few emails because it gives you more time to think about what you are going to say and to get a feel for the other person. Once you get more familiar with each other, then you can start chatting.

If you don’t have a paid membership, you’ll most likely be limited to using ‘winks’ or ‘smiles’ or something similar. These are canned messages that will say something like “Nancy is interested in you” or “Joe winked at you”. Winks and smiles are a quick way to say hello but drastically limit your ability to pique someone’s interest. This puts a lot of pressure on having a terrific profile because it will have to do all of your talking for you.

Email is best in the beginning.

Emailing a potential date is a lot like flirting. The purpose of the first email is to get them to respond, to open a dialogue. You want to get their interest but leave it open-ended so that they will respond back to you. Keep your emails short and charming. Another tip: don’t send a barrage of emails to one person, follow their pace, and try to keep up. (If they send 4 a week, you send 4 or so a week.)

So How Do You Write That First Email?

When replying to personal ads, try to be, well, personable. Write at least a paragraph or two about yourself and what you like about them or their personal ad. Many of the principles of profile writing apply to emails, such as staying positive, being honest, and paying close attention to spelling and grammar.

Meeting someone online is very exciting and can make you feel like a love-struck teenager, but do your best not to sound like one. Most of us are looking for someone that is a little more mature, someone that has the potential for being a lifetime partner. When you first start communicating with a person, there is nothing wrong with flirtation, being happy, and laughing, but make sure it’s not over the top. Also, don’t start by pouring out your soul, telling him or her all about your ex-spouse or ex-significant other. Avoid talking about personal things such as financial problems, health issues, or stories about your dysfunctional family. This is a huge turnoff, and an excellent way to scare someone away. Save that kind of talk for your Thursday night poker game or day at the hairdresser. If you are a single parent, a little bit of conversation about your kids is fine to break the ice and find common ground, but remember you are trying to build a romantic connection, so keep it to a minimum.

Always be honest!

If the relationship moves forward, the truth will come out eventually. It’s far better to be yourself upfront rather than tell a silly lie in the beginning, only to be found out and have a potential relationship fall apart.

Keep it positive!

The last thing anyone wants is to send a message to someone and in the response, hear all about their past failed relationships, health problems, or financial woes. You can share the doom and gloom after you get to know each other a little bit. Or better yet, just put all that stuff behind you and move on. There’s no time like the present to start fresh!

Compliment something you found interesting in their profile.

This is where it’s important to read the person’s profile. It gives you things to talk about. For example, if you are a woman and you find a man interesting and he has Labrador dogs just like you, you could say something like, “Hi. My name is Mary and I noticed in your profile that you have Labs. I do too!” From there, give a brief description of your dog, mention that you would enjoy hearing back, and sign off.

Avoid overtly sexual comments.

Don’t come on too strong at first with sexual innuendos and try not to comment on the person’s photo. Find something a little more ‘deep’ to comment on, maybe something they said in their description.

Find a way to continue the communication.

The main point of the first email is to get them to notice you and to respond back to you. Don’t give up too much information, but tell them enough to get them interested. You are trying to get a conversation going, so asking questions is a good idea, as long as you don’t ask too many.

Mention things you have in common, and ask a question or two about them.

For example, when you first start messaging with someone, you could ask, “Did you do anything fun this week?” “Do you have any great plans for the weekend?” This will help you learn more about the person without seeming nosey. After you have been communicating with someone special for a while, you can use innocent questions to see if you can find an opening in time when the two of you might meet.

Try to avoid long letters with little details that might be considered boring.

Keep it to the point, but try to let your personality shine through. Then, a good rule of thumb is “compliments and questions.” An earnest compliment on the person’s accomplishments, writing style, or life goals will say a lot.

Here are a couple of good, ice-breaking starter topics:

If you live in the same area, comment on the area, or something relating to it. If you don’t live in the same area, you can ask questions about where they are.

Music and movies are also a good conversation-starter; almost everyone likes some kind of music or movie.

Maybe you went to the same college or better yet, a rival school. Poking fun at rival schools is always a fun way to break the ice.

And sign your real first name…

If you work this right, the person will contact you back. Remember, even if you get a response, you’ll have to keep their interest. In the emails that follow, keep asking questions and keep complimenting (while remaining honest and positive). When you feel comfortable, you can move on to more intimate forms of communication like instant messaging, the telephone, and eventually, meeting in person.

If a day goes by and you haven’t heard from them, rather than inundate the individual’s mailbox with messages, leave one short, sweet message that provides a small hint to prompt him or her to reply.


Don’t give out your full name, personal email address, or phone number in this initial email; wait until you’re both interested and it’s apparent that it’s going somewhere.

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