Online Dating Etiquette: The Do’s and Don’ts of Messaging

Online dating is a lot like a job search. For every job there are hundreds of applicants submitting their resumes and cover letters. For a truly good job with excellent benefits, there are hundreds of interested candidates. Would you send in a sloppy resume and a one sentence cover letter to apply to your dream job? Would you blanket the market with a generic cover letter in the hopes that somebody gets back to you? In job searches as well as online dating, you have one shot at making a good first impression. If you succeed, your prospective match will look at the rest of your application. How do you write your message to make that all important first impression?

Introduce yourself. When you apply to a new job, you would start by telling your prospective employer a little bit about yourself in the cover letter, right? Say your prospective match is an environmental activist. You would say, “Hi, my name is Tim and I work in a nonprofit that helps children. We work on a lot of cases of families that are impacted by climate change.” Just your name and something you have in common are  enough. Providing the basics is 1) respectful because it doesn’t assume that she’s read your profile 2) announces that you are a member of society, 3) shows confidence.

Identify commonalities. When you read her profile, notice what are her passions. What are the things that are most important in her life? What are her goals and interests? The more you can align yourself with the things that are important to her, the more likely she will be interested in you. For example, if she volunteers for an animal shelter and has pictures of herself with pets, say, “I notice that you love working with pets. I got my dog from a rescue agency in Chester County. He was six months old when I got him and timid as a mouse, but now he’s the king of the house! Where did you get yours?” Boom! You have found a way to relate to her and opened the conversation for something she loves.

Share a hook: If you have a mutual interest in writing, you could say, “I’m also interested in writing and I’m currently working on a screenplay. What do you write about and do you share any of your work online?” When you say “I’m currently working on a screenplay,” that’s a hook that the other person can ask you about. Make sure that it’s a hook that she could respond to. For example, if she mentioned that she enjoys the beach, you might share, “My sister had her wedding on the beach. We had a guitar band after dark, and the next day we got to hang out at the beach with all her friends. It was so much fun!” Share these little teasers so that the other person has something to ask about you in addition to answering your question about her.

Ask a question related to her interests: Asking a question shows that you’ve read her profile and gives her something to respond to. Asking for recommendations is an excellent way to do both. If she likes to read fan fiction, what are her most recommended titles? If she’s a foodie, what are her favorite local restaurants? If she’s an outdoor enthusiast, what are the best places for hiking in the region? Do not ask her overly personal questions in the first message such as her job title, her religious or political affiliation, or what she’s looking for in a man; unless she shared those things in her profile and you have those things in common. Also don’t ask questions like, “How was your weekend?” or “How’s online dating working for you?” She doesn’t know you yet and has no need to talk to you as if you were her best friend.

You don’t need to write a long letter sharing your philosophical musings about love and life in the middle of the night. You don’t need to shower her with compliments. You don’t need to provide your resume or list your personality traits. Just a paragraph politely introducing yourself, identify your mutual interests or commonalities, share a hook, and ask her a question.


Ok, you pressed Send! Now what?

If she writes back with a polite rejection, be grateful for the acknowledgement, you don’t need to reply, and move on.

If you’ve waited two days and she hasn’t responded, don’t write back, “Hello? Did you get my message?” hoping that it’ll prompt a response. They are not your employee and not obligated to respond to you. In fact, they are more like the employer; they don’t have to respond to anyone they are not interested in hiring, and inquiring after your application will get you black marks.

If you get passed over, don’t take it personally. Some people only check their online dating inbox once a week. God knows we all have enough messages that we HAVE to respond to. Maybe she’s busy and not really interested in responding to anyone this week. Maybe she got a lot of messages and overlooked yours. Maybe she looked at your profile and determined that you were not a good fit. In a job search, the employer may shortlist your application, but if they don’t want to interview you, they are not going to contact you. It’s nothing personal, you’re just not the right fit. Move on. If you feel that you have a lot of commonalities with this person and there could really be a connection, then gently check back a week later and say, “If you’d like to chat, I’m still interested in hearing from you.” If they don’t respond, assume they pass. Move on.

If she writes back with interest, now it’s up to you to turn her interest into a date. You can continue to discuss the subject that is of interest to you both, or you can discuss another commonality:

“Hey! Thanks for your book recommendations! I’ll be sure to check them out. I love One Hundred Years of Solitude. Have you read Love in the Time of Cholera by Gabriel Marquez?”

“Hey! Fairmont Park also hosts great concerts in the summer. Do you like outdoor concerts?”

At this point, you need to turn this interaction into an in-person meeting as quickly as possible. A few back and forths are fine, but with each new round the person has a chance of backing out or losing interest. Suggest a time and place near her (not near you) to meet up. “I’d love to talk more about this with you in person. How about meeting me at Green Engine Coffee on Tuesday at 8pm?” Don’t leave it to the other person to suggest a time or place, even if you think you are just being accommodating. Take the initiative and make it simple for the other person to accept.

Once she accepts a date, give her your number. If she responds with hers, send her a text the day before you meet up to confirm.


So now that I’ve covered the Do’s of messaging, what are the Don’ts?

Don’t send blanket messages: It’s easy to detect blanket messages and women get a lot of them. A carefully crafted personalized message shows that you actually care about the person and are interested in her, which will make her more likely to be interested in you.

Don’t write one word or sentence: You cannot properly introduce yourself in one sentence much less do all of what I described above. A message such as “Hi,” “How are you?” or “You’re beautiful and I’d like to get to know you” shows a lack of confidence and puts the burden of starting a conversation on the other person. Take the initiative and engage her in a topic that interests her.

Don’t compliment her appearance: Saying how great her photo looks or complimenting her with words such as “beautiful,” “sexy,” “attractive” shows that you only looked at her photo and not her self description. If you do want to pay compliments, compliment her on her interests or something specific in her profile.

Don’t write a long message: The ideal message is one or two short paragraphs. Don’t tell her your life story. If the message is too long it makes you appear 1. naive (why would you spend so much time writing to someone you don’t know?) 2. desperate (do you have nobody to talk to and nothing else to do?) 3. entitled (as if you expect that the other person will respond).

Don’t get emotional: It’s ok to say, “It seems like we have a lot in common,” or “I resonate with what you have to say,” but if you say things like, “I think we’re soulmates,” or “you look like my next girlfriend” when you haven’t even met the other person, you need to get off-line and see a therapist.

Don’t ask too many questions: One or two is enough to get a conversation going and establish if she’s interested in talking to you at all. Save the rest of your questions for a real date.

Don’t keep messaging if she doesn’t respond: If she has decided she’s not interested in you, continuing to message her will be taken as harassment.

Don’t be a pen pal: Three to six messages is all you need to move the conversation to in-person. Sending lots of messages back and forth is a waste of time because if you do meet up eventually, you may find that you don’t actually connect, and with every round of messages you risk her losing interest. If you’re long distance and can’t meet up soon, have a phone or video call early so that you can decide whether or not you want to keep chatting.

Finally, remember that you are the applicant looking for a job. If you want to stand out from the crowd, sell yourself well. Use proper grammar. Be polite, warm, patient, confident. Be sincere, because the person whose interests are aligned with yours is more likely to find you attractive too. And don’t take it personally. You may meet the love of your life online, you may meet a friend, or you may meet no one. But really, you have nothing to lose. You’ll never win if you don’t play, and winning can be pretty sweet in this instance.

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