The usual problem for an older man on a dating app is a first message that is too long, too formal or too forward. In 2023, only 20% of Americans aged 50 to 64 told Pew Research Center they had ever used a dating site or app, which means many men in that group are writing flirtatious messages to strangers on a phone screen for the first time in their lives.
Opening Lines Tied to Her Profile
A first message that could go to anyone looks like it went to everyone. One specific detail from her profile, followed by a question she can answer in a sentence, gives her something to reply to. If her photos show a surf beach, “Is that Bells Beach or somewhere quieter?” gets further than “You have a lovely smile,” because a compliment on appearance leaves her nothing to answer except thanks. Her profile usually offers more than one hook, and picking the less obvious one, such as a book visible in a photo instead of the beach behind her, shows that he read it.
A mild tease about something she wrote, such as a claim to make the best pavlova in Brisbane, invites her to defend it, and that back-and-forth is the flirting. It needs no mention of her looks at all in the first few messages.
Message Length and Pace
Men who learned to write in letters and email often send paragraphs. On a phone, a message of more than 3 or 4 lines takes real effort to read. A 2018 study of messaging data from 4 US cities, published in Science Advances, found that effort put into writing longer messages was largely wasted in terms of replies. The one exception the authors noted was Seattle, where men writing longer messages to more desirable women did somewhat better.
Replying within a few hours is normal, while answering every message within 30 seconds can look anxious. Matching her rhythm roughly, and leaving a conversation until the next day when it slows, keeps things relaxed.
Stated Intentions in the Profile
Flirting is most awkward when two people want different things and neither has said so. A profile that states the goal plainly settles much of that before the first message is sent.
Men on apps list goals such as remarrying or regular company for dinners and holidays, and some state the hope to find a sugar baby. Naming his own in a sentence or two means the women who reply already know it.
Spelling and Formality
Tess van der Zanden and colleagues at Tilburg University tested how typos in a profile affect first impressions, with participants whose average age was 55. In the first study, 373 Dutch users rated profiles with and without language errors, and the profiles with errors were rated less socially and romantically attractive. The effect came mostly from the 33.5% of participants who noticed the errors, and for them the damage was large.
A second study separated the kinds of error. Mechanical slips, such as “teh” for “the,” were taken as a sign of inattention, and grammatical mistakes as a sign of lower intelligence. Informal language, including abbreviations and heavy punctuation, was linked to lower warmth. Full words and a quick proofread before sending avoid both problems. Text-speak borrowed from younger users adds to them.
Emoji in Early Messages
The Kinsey Institute team that studied emoji as affective signals surveyed 5,327 single American adults in 2019. Of those, 28.2% regularly used emoji with potential dates and 37.6% never did. The more frequent users went on more first dates and were more likely to see a date a second time, although the design could not show cause and effect.
The Tilburg and Kinsey findings apply to different settings. The Tilburg work looked at profile text, and the Kinsey work looked at messages between people already talking. A single emoji after a dry remark tells her the remark is a joke, which matters for a man whose humour could otherwise be taken as rudeness.
Talking About the Past
By the third or fourth exchange, the questions turn to his history. A divorce, a late wife or grown children are ordinary facts for a man in his 50s or 60s. Australian courts granted 48,700 divorces in 2023, and the median marriage had lasted 13 years, according to Australian Bureau of Statistics figures on Australia’s marriages and divorces reported by SBS. A single plain sentence covers his own part in those numbers. The awkward version is a long account of what went wrong in a marriage, or a complaint about an ex, sent to someone he has not yet met.
The same restraint applies to his career. One detail that says something about him, such as the job he left at 52 to run a vineyard, is easier for her to ask about than a list of titles.
Compliments and Boundaries
Pew Research Center’s 2023 key findings on online dating in the United States show what many women receive. Among women under 50 who had used a dating site or app, 56% had been sent a sexually explicit message or image they did not ask for, and 43% said someone kept contacting them after they said they were not interested.
Physical compliments, if any, can wait until after a meeting, and a “no thanks” or a week of silence ends the conversation. The same survey found that 64% of men who had recently used these services had felt insecure about how few messages they received, so a silence is common and says little about the man.
A Short Plan for a First Meeting
After several days of steady replies, a longer text exchange adds little. A short, specific suggestion, such as coffee on Saturday morning near her suburb, is easy for her to accept or decline. An open question like “Would you like to meet up some time?” puts the planning on her.
A public place and a time limit of about an hour make the first meeting easy to agree to. If she prefers a short video call first, that request is common and reasonable, and agreeing to it without fuss is part of not sounding awkward.
Desirability at 50
The Science Advances study that questioned long messages also found that men peak at 50 in desirability on a dating site, measured by who received messages and from whom. A man in his 50s who sends awkward messages gives away an advantage the data says he already has, and a careful message keeps it.
