Plenty of Fish recommends keeping a first message upbeat, short and sweet. Read her page before you write, refer to her hobbies, pictures or interests to find common ground, compliment something on her page rather than her looks, and leave out pet names like cutie, babe or honey.

Short and upbeat does most of the work

POF's first piece of advice is the one men ignore most: keep it short.

A first message is not a cover letter. She does not know you yet, and a long paragraph from a stranger asks her to do a lot of reading before she has decided she cares. a dating coach's rule for messaging is that if you can say something in fewer words, fewer is better. One or two lines is plenty.

Upbeat matters just as much. A message that opens with a complaint about the app, a sigh about how dating is hard, or an apology for writing at all sets the mood of the whole conversation. Open on something light and she is more likely to answer in the same spirit.

Read her page before you type

POF tells you to read her profile first, and it is the step that separates a real message from a mass one.

My own process begins there too. Right after a match, he reads through everything she has put on her page, hunting for one odd or unexpected detail, ideally something he can gently make fun of. It might be a strange line she wrote, a specific place in a photo, or a hobby few people have. That detail becomes the message.

If you cannot find anything, look harder before you settle for "hey." Almost everyone leaves something to work with.

Her interests beat her looks

POF suggests complimenting something on her profile rather than her looks. This is the part of the advice most worth taking seriously.

Her looks are the obvious thing to mention, which is exactly why a message about them blends in with all the others that mention them too. It also hands her nothing to say back except "thanks."

Her interests are different. They are things she chose to share, so noticing them tells her you paid attention. And they are easy to answer, because she already has opinions about them.

coach adds a useful refinement. In his experience, commenting on something she wrote usually lands better than commenting on a photo, because it reads as more genuine and less superficial. Pictures still count, as POF says. Just comment on what is happening in them, like the trip, the dog or the terrible karaoke, rather than on how she looks in them.

Leave the pet names out

POF specifically says to skip pet names like cutie, babe or honey, and it is right.

From a stranger, a pet name assumes a closeness that does not exist yet. It also reads as a line you could send to every woman on the app without changing a word, which is usually exactly what it is. Use her name, or no name at all.

Where POF's advice stops short

POF's tips will keep you from sending a bad first message. On their own, they will not make yours stand out.

Short, friendly and specific describes a lot of forgettable messages. What coach adds is a little edge. He likes to be slightly irreverent, a bit cocky and a bit funny in his first line, often by teasing her about the thing he noticed rather than simply praising it. A light jab invites her to defend herself, and a woman defending her taste in music is already talking to you.

He also keeps a small set of openers that have worked before for particular kinds of women, and reuses them when he has nothing better. There is no need to reinvent the message every time.

What a good opener looks like

Put POF's rules and My edge together and you get something like these, each built on one real detail:

  • Her page says she is training for a half marathon: "Training for a half marathon on purpose? I need to hear the reasoning."
  • One photo shows her at a ramen counter: "You look like someone with strong opinions about ramen. Best spot in town, go."
  • She lists hiking and bad reality TV: "Hiking and reality TV is a dangerous combination. Which one wins on a Sunday?"

Each one is short, upbeat and about her, with no comment on her looks and no pet name. Each one is easy to answer in a single line.

After she answers

A first message only has one job, which is to start a conversation. Once it has, keep that conversation short and moving toward a plan.

From there, coach keeps it playful and lets her learn a few true things about his life. That builds enough comfort that suggesting a drink feels natural rather than sudden, and once she agrees he swaps numbers or WhatsApp to settle the details. The opener earns you a reply. The handful of messages after it are what turn that reply into a date.