If you want to ask a woman out when you work together, check whether your workplace permits the relationship, make sure neither of you has authority over the other's job, and look for clear, mutual personal interest outside ordinary work duties. If the circumstances are appropriate, make one discreet, straightforward invitation where she can decline comfortably. Accept the answer completely and keep the working relationship professional. Where one person manages, assesses or controls the other's opportunities, the safest course is not to pursue the invitation.
There is an excellent reason romance and office stationery should be kept separate: both become surprisingly difficult to retrieve once somebody has put them through the shredder.
I learned this at a publishing house where a gentleman named Felix worked in editorial production. He was smitten with a colleague called Arabella, who managed the picture archive.
Felix had composed a letter of such florid beauty that it mentioned moonlit gardens, eternal devotion and the possibility that their descendants might inherit his grandfather's Victorian gramophone.
He intended to deliver it during the Monday production meeting.
“Felix,” I said, “the woman is coming to discuss the magazine's cover photographs. Why are you planning to announce the future of your bloodline?”
He looked injured.
“It's romantic.”
“It is also twenty-seven lines long and likely to be read while the finance director is taking notes.”
A workplace can introduce two adults who genuinely enjoy one another. But it also creates responsibilities that don't disappear because somebody has magnificent eyes.
Before you ask: who has power over whose job?
This is the first question, not the last.
If you're her manager, decide her shifts, influence her promotion, supervise her performance or control her pay, a romantic invitation can carry pressure even if you don't intend it.
Likewise, if she's your manager, consider whether either person's professional choices could become entangled with a relationship.
CIPD guidance on workplace relationships highlights risks such as favouritism, conflicts of interest and particular concerns about manager–junior relationships.
Don't tell yourself the problem is solved because you promise to be charming about it.
If there's a direct reporting relationship or another significant imbalance of power, don't pursue a date under that arrangement. Seek appropriate workplace advice about conflicts and policies rather than asking somebody who depends on your professional decisions to assess your romantic appeal.
Two colleagues of similar seniority who don't supervise each other may be in a different situation. Even then, discretion and genuine mutual interest matter.
Romance should never become another item in a person's performance review.
Read the workplace policy before you write the invitation
Some employers have specific policies about staff relationships or conflicts of interest. Others deal with issues through more general conduct, harassment and disclosure procedures.
Don't assume that because you've seen colleagues dating in another company, the same arrangements apply in yours.
Read the relevant handbook or policy. If needed, ask HR about general expectations without sharing a colleague's private life or announcing an imaginary relationship.
Avoid treating the absence of a specific rule as permission to pursue people repeatedly at work.
And never use access to personnel information, internal calendars, contact databases or company devices to obtain somebody's private details.
A work email address is for work. An employee's personal telephone number, if provided for professional reasons, is not a secret romantic prize.
If somebody wants you to contact her outside work, let that arise openly and voluntarily.
Don't mistake professional warmth for flirtation
Arabella laughed at Felix's jokes in meetings. She asked whether he'd had a pleasant weekend. She once brought him a slice of birthday cake.
He considered this a conclusive declaration of attraction.
“My dear chap,” I said, “she also brought cake for the accounts department. Are you proposing to the entire payroll team?”
Friendly colleagues can be particularly kind because they spend so much time together and want a pleasant working environment.
A shared joke, helpfulness on a project or an enthusiastic conversation about the office coffee machine may simply mean she likes you as a colleague.
If a genuine friendship develops beyond work — perhaps you both voluntarily spend time with the same group of friends or talk about shared hobbies — romantic interest might become clearer.
But don't assume. And don't conduct a campaign of suggestive jokes in the workplace to see whether she eventually responds.
An employee shouldn't have to manage somebody else's romantic experiment while trying to earn a living.
What a discreet invitation actually looks like
Suppose you're peers, neither person has authority over the other, the employer's expectations permit it and you've become genuinely friendly.
You might speak during an ordinary, comfortable moment away from an audience, but not in a secluded place where she can't easily leave.
“I've really enjoyed getting to know you. Would you fancy going to the photography exhibition with me on Saturday, as a date?”
It's one invitation, with a clear purpose.
Don't deliver it during a deadline crisis, in a meeting, through a company-wide chat or while she's carrying boxes of work to her car.
And don't make it an office spectacle. If colleagues gather round, laugh or urge her to accept, the freedom to say no becomes considerably less comfortable.
She may say yes, no, or that she'd rather keep things professional.
Any of those answers deserves respect. You are offering a possibility, not presenting an application she has to approve.
A refusal means the subject is closed
This point is more important at work than almost anywhere else.
If she says no, don't ask again after a fortnight. Don't request a written explanation. Don't enlist colleagues to argue that you're a wonderful catch.
Say something simple: “Of course. No problem.”
Then continue behaving professionally.
Don't withdraw cooperation, turn cold in meetings or begin treating her as though she has personally betrayed you.
You may need to manage your own disappointment, but she must be free to do her job without becoming responsible for your feelings.
Even if her reply is uncertain, avoid repeated pressure. One clear invitation is enough.
If she chooses to revisit the idea herself later, she can do so. Until then, assume your normal workplace relationship continues.
The dignity of a gentleman is most visible when the answer isn't the one he wanted.
Felix abandons the Victorian gramophone
Felix was a production editor and Arabella worked in another department. Neither supervised the other.
Before doing anything, he checked the company's relationship guidance. Then he stopped interpreting every meeting as a romantic omen.
They'd both become interested in a public exhibition about old illustrated magazines. They had discussed it over lunch with several colleagues.
One Friday, away from a work meeting and without an audience, he asked whether she'd fancy visiting it with him.
He didn't mention the gramophone.
Arabella said she hadn't thought about the two of them that way, and would prefer to keep things friendly.
Felix thanked her for being clear.
The following Monday they discussed the cover photography as usual. He didn't become hostile or start distributing speeches about heartbreak.
Several months later they remained friendly colleagues. Their jobs were intact, and the entire office had been spared a dramatic incident involving the stationery cupboard.
No romantic triumph, perhaps — but an impressive display of good manners and adult judgement.
What if the interest really is mutual?
If two colleagues choose to date, they should discuss practical boundaries rather than behaving as if the workplace has disappeared.
How will you handle work conversations? Are there disclosure requirements? Could a reporting relationship or project assignment create a conflict?
Check the actual employer policy and seek appropriate HR guidance where necessary.
Keep professional decisions separate from the relationship. Don't favour a partner when allocating work, and don't punish them during a disagreement.
Workplace meetings aren't the place for private arguments or displays of affection that make colleagues uncomfortable.
If the relationship ends, both people still have responsibilities to the wider team.
You can be romantic, old boy, without turning the sales department into a touring production of Romeo and Juliet.
What about an office party?
An office social is not automatically an invitation to pursue colleagues.
People may be relaxed, dressed differently and laughing more than usual. That doesn't turn their professional relationship into a romantic commitment.
Alcohol can also complicate judgement.
Don't use a party as an excuse to corner a colleague, make explicit comments or assume a dance means further attention is welcome.
If you already have a genuinely mutual personal connection and the circumstances are appropriate, an invitation at another sober, comfortable moment is likely to be clearer.
And do not allow colleagues to place bets on who will leave together.
A good workplace party should produce amusing memories, not formal complaints.
When it may be better not to ask at all
Sometimes the wisest romantic decision is to leave an attraction unpursued.
You may work on a tiny team where the other person couldn't reasonably avoid you. You may be responsible for her career progression. She may have already indicated that she doesn't date colleagues.
Perhaps you're not sure you could cope professionally with a refusal.
Those are reasons to reconsider, not challenges to overcome with a better opening line.
You can remain courteous, enjoy the working relationship and meet women elsewhere — through friends, classes, events or dating services.
It is entirely possible to admire someone without needing to convert that admiration into a proposal.
And there's nothing unmanly about choosing professional peace over a potentially uncomfortable situation.
Monty's final note for the office romantic
Felix eventually met a woman at a weekend heritage event. Their first conversation involved an antique printing press and a spectacularly jammed ink roller.
He told me he'd learnt more from one straightforward invitation than from his entire proposed letter about eternity.
I agreed. Then I demanded to see the letter, because twenty-seven lines about a gramophone should not be allowed to disappear from literary history.
A good workplace invitation is discreet, genuinely optional and rare. A good workplace remains comfortable even when the answer is no.
If the circumstances aren't right, seek your romance beyond the office. There are plenty of delightful women in the world who have no need to review your quarterly performance figures.
For more of Monty's particular brand of courtship, the complimentary introductory guide is available through the offer below.