Starting again
Your first date in twenty years
The mechanics have changed. The evening itself has not, and that turns out to be the reassuring part.
If your last first date was in the nineties, the unfamiliar bit is everything up to the date. Once you are sitting across from someone, it is the same as it ever was — two people working out whether they want to keep talking.
What has changed
| Then | Now |
|---|---|
| A phone call to arrange it | Messages, and usually a short video call first |
| Dinner, often | A drink or a coffee, usually an hour or two |
| You knew someone who knew them | Usually no shared context at all |
| Waiting days to hear back | Replies within hours, and silence means no |
| Getting ready for an evening | Same, except everyone now assumes you will look roughly like your photographs |
The move from dinner to a drink is the useful change. A meal commits you both to two or three hours regardless of how it goes; a coffee can pleasantly last forty minutes or extend all evening. Nearly everyone now suggests the shorter option first, and it is not a lack of enthusiasm.
The video call
Ten or fifteen minutes before meeting is now standard practice. It exists to confirm that the person is who they say they are, and it is entirely normal to ask for. Anyone reacting badly to the suggestion has told you something useful.
The first twenty minutes
Which is the part people dread. Some things that help, from people who have done it recently:
- Arrive first and get a drink. Being settled beats walking into a room.
- Say plainly that you are nervous if you are. It almost always produces the same admission back, and the evening improves immediately.
- Have two questions ready that are not about work.
- Do not rehearse. Rehearsed answers sound rehearsed and the conversation goes somewhere else anyway.
- Agree a rough end time with yourself. Knowing there is an exit makes the whole thing easier.
What to talk about, and what to leave
Ordinary things. Where you live, what you do at weekends, where you have been, what you are looking forward to. The conversation people remember well is almost never the profound one.
Worth leaving for later: the full account of your divorce or bereavement, money, and anything that needs a defence. Mention them if they come up, briefly, and move on. Everyone at this age has a history and nobody wants it over a first drink.
Afterwards
Say if you would like to meet again — that evening or the next day, not three days later. The waiting game is largely gone and being straightforward now reads as confidence rather than eagerness.
If you would not, a short message is kind and takes ten seconds. Silence is common and it is not what you would want.
The most common thing people say afterwards is that it was far less alarming than the fortnight of anticipation beforehand. The anticipation is the hard part, and it only ends by going.
Common questions
What should a first date be now?
A drink or coffee, an hour or two, somewhere public. The long dinner has largely gone because it commits you both regardless of how it goes.
Should I do a video call first?
Yes, it is now standard. Ten or fifteen minutes confirms the person is who they say they are, and nobody reasonable objects to being asked.
How soon should I say I want to see them again?
That evening or the next day. The three-day rule is gone and directness now reads as confidence.
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Last updated: July 2026