Questions to Ask Yourself Before Dating
Twenty questions for the point just before you start dating, or start again. They cover what you want from the next six months, how much time and attention you actually have, what you will be honest about early, and what you would end things over.
The questions
Open any question for the note
Why now? What changed in the last month or two?
Why ask it
A specific trigger is worth naming: a birthday, a friend's wedding, an ex moving on, a quiet winter. None of these are bad reasons, but knowing which one is driving you predicts how patient you will be in the first few weeks.
How long has it been since my last relationship, and am I still in contact?
Why ask it
Ongoing contact is not automatically a problem, but it changes what you can offer someone new. If you would hide those messages from a person you had been seeing for a month, that is the answer.
Is there anyone I would drop this for if they came back?
Why ask it
An uncomfortable question with a clear use: if someone is being kept in reserve, everyone you meet is auditioning against a person who is not in the room. Better to know that now than to explain it in six weeks.
What am I looking for over the next six months: company, sex, a relationship, or a partner to build with?
Why ask it
Six months is short enough to answer honestly, unlike questions about what you want in life. Any of these answers is fine; the problem is only when someone gives one answer and hopes for another.
Could I say that out loud on a second date?
Why ask it
If your honest answer would embarrass you, you will probably soften it, and softened answers waste months of two people's time. Practicing the plain sentence now makes it much easier to say when it matters.
Whose opinion am I doing this for?
Why ask it
Parents wanting grandchildren, a friend group where everyone is paired off, or an ex you want to have moved on from. Dating on someone else's schedule tends to produce a relationship you defend rather than enjoy.
How many evenings a week can I actually give this?
Why ask it
Look at your real week, including work, family, training, shifts and the nights you need alone. People with one free evening every two weeks can still date, but they should know it and say it rather than seeming uninterested.
What would I have to stop doing to make room?
Why ask it
Something has to give: gym sessions, a hobby, time with friends, evenings with the children, sleep. Deciding in advance what you will trade stops you resenting the new person for a squeeze you chose.
What do I do when I start to like someone?
Why ask it
Most people have a pattern: texting constantly, going quiet to seem unbothered, rearranging their week, or losing interest as soon as it is returned. Naming yours is worth more than any list of what you want in a partner.
How do I behave when I am not sure where I stand?
Why ask it
This is where dating actually gets difficult, and the honest answer is often waiting, checking, or asking friends to interpret a message. If your instinct is to guess rather than ask, decide now what you will ask and when.
What did the last person who ended things with me say about me?
Why ask it
You do not have to accept their view, but it is the only outside account you have. If two people said the same thing, that is worth more attention than anything you would put on a profile.
If I described myself honestly as a partner, what is the difficult part?
Why ask it
Long hours, a demanding family, a short temper in the mornings, a habit of withdrawing. Knowing your own hard edge lets you mention it early instead of hoping it stays hidden until someone is attached.
What do I need to be honest about in the first few weeks?
Why ask it
Children, a marriage that has not legally ended, religion, monogamy, money, a health condition, whether you plan to move. These are all easier to say at week two than at month four, and delay is what turns them into betrayals.
What are two things I would end it over, and have I ever actually walked away for either?
Why ask it
Stated limits mean little without a record. If you have overlooked the same thing twice before, plan the specific action, not the principle: what you will say, and by when.
Am I hoping someone will solve something specific?
Why ask it
Loneliness, rent, childcare, a visa, boredom, an unhappy home. It is not wrong to want a partner to make life easier, but a relationship taken on to fix one problem tends to be judged only on that, and then resented for it.
What have I not told anyone about how my last relationship went?
Why ask it
The unsaid part is usually where your own behavior sits, or where something was worse than you have admitted. You do not have to tell a date, but you should be able to tell yourself, or it will repeat quietly.
Who will I talk to about the people I meet, and do I want their running commentary?
Why ask it
A friend who mocks everyone you mention, or a parent who asks about marriage after two dates, changes how you behave. Choose one person to talk to and consider keeping the early weeks otherwise private.
What am I not willing to accept in the first month?
Why ask it
Late cancellations, replies after midnight only, being kept away from their friends, pressure for sex or for exclusivity. Decide the line before you meet someone you like, because in the moment everything is negotiable.
A few dates in, what will I be looking at to decide whether to continue?
Why ask it
Pick two or three observable things: whether they ask you questions, how they treat staff, whether plans happen when they say they will, how you feel on the walk home. Otherwise the decision gets made purely on nerves and attraction.
If nothing comes of this for a year, will I be all right?
Why ask it
The honest answer shapes everything else. If a year of no relationship would be genuinely bad for you, the work is on building the rest of your life at the same time, because that pressure is visible to the people you meet.
Getting Ready to Date
Practical guidance for the conversation itself
Worth Doing First
Say what you want, early and plainly
One sentence on the first or second date about what you are looking for saves months. It also filters faster than any profile wording, because people respond honestly to a direct statement more often than to a hint.
Check the practical mismatches before the emotional ones
Children, location, monogamy, religion and whether either of you wants marriage are not compatibility subtleties; they are yes or no facts. Asking in the first couple of weeks feels blunt and prevents the worst kind of ending.
Keep your own week running
Do not cancel the class, the friends or the training for someone you have met twice. It protects you if it ends, and it makes you better company while it lasts.
Notice how you feel afterwards, not just during
The walk home is more informative than the date. Relief, flatness or a need to reread the conversation to check you did well are all worth recording, because you will forget them by the next time they text.
Take basic precautions when meeting strangers
Meet somewhere public the first time, tell one person where you are going and when you expect to be back, arrange your own way home, and do not leave a drink unattended. A short video call beforehand also confirms that a person is who their photographs say.
Two Short Exercises
A readiness check, fifteen minutes on paper
- 1Write what you want from the next six months in one sentence.
- 2Write how many evenings a week you can give it, and which ones.
- 3Write the two things you would end it over, and what you will say if they happen.
- 4Write what you need to disclose in the first few weeks.
- 5Write one thing you did in your last relationship that you would rather not repeat.
- 6Read it back and cross out anything you would not be willing to say out loud.
What to cover, and roughly when
- 1First couple of dates: what you are each looking for, in general terms.
- 2First few weeks: children, whether you are seeing other people, where you live and whether you plan to stay.
- 3Around the point it becomes regular: exclusivity, sex and contraception, and how you each handle disagreements.
- 4Before it becomes serious: money, family expectations, religion, and health issues that would affect a partner.
- 5At every stage: whether the answers you are getting match the behavior you are seeing.
Common Traps
- Dating to prove something after a breakup. It is a common reason to start, and it usually costs someone else a few months.
- Auditioning instead of noticing. Spending a date working out whether they like you leaves no attention for whether you like them.
- Talking about an ex at length. Some context is normal; a running account tells a new person exactly where your attention is.
- Treating a checklist as compatibility. Height, job and hobbies are easy to screen for and predict very little about how two people get on.
- Asking for commitment while quietly keeping options open. Whatever the intention, it is the behavior that gets remembered.
- Deciding after one date. First meetings favor the confident and the well-practiced, so unless something was actually wrong, a second is usually a fairer test.
- Waiting to feel completely ready. Nobody arrives fully prepared, and the useful question is whether you can be honest about where you are, not whether you have finished working on yourself.