Caitlin is a very attractive woman in her late thirties. The classical blonde, slim but with generous curves in the right places, and endowed with genes that will let her look 28 for a while still. She is as smart as she’s hot, with an Ivy League MBA, and working long hours. She has strong values and is beautiful on the inside too. The one thing she finds missing from her life is – a better half. She would like to marry, and she knows what kind of guy she is looking for. But not too many people are showing up, and she has not been happy with those who have. People who know her are puzzled that she, of all people, should still be single.

Caitlin is not a rare case among my acquaintances. I too am puzzled. But let’s take her case as an example and try to find avenues for love to enter her life.

1. Work Less (and Better). Caitlin is single, without dependents to care for, and still her life is packed packed packed with barely a minute to spare. No. 1 reason: work. Caitlin works hours that are totally incompatible with a regular dating life let alone a family life. She needs to stick to the timetable in her contract, and make use of leave time, holidays, compensatory leave for long hours or weekends worked – whatever her employer’s rules allow. And she needs to study these rules and find out, and put her foot down if needed. Downtime is good for dating, and good for productivity at work. (The Economist says: she needs to reveal her true work-life trade-off preferences.)
2. Use Your Work Hours Well. Of course the main focus of her work hours should be her tasks and professional goals. It may however be in the interest of her professional life to cultivate a network of peer experts for exchange and review, or to take group training, whether in leadership, a language, organizational skills or something else. These activities kill two birds with one stone; they promote professional development and foster personal encounters. Caitlin’s dream date may attend one of the trainings, or be a peer expert, but even if not, there may be a person who knows someone Caitlin should know.
3. Meet Many Quality People. Twelve should suffice, but more doesn’t harm. In order not to waste her precious time, Caitlin should focus on social circles and activities that likely attract people with her core values. If she is an environmentalist – she should find the key environmental groups and events in town and attend them. If she practices a religion – she should attend their singles groups or affiliated dating agencies. ALL OF THEM. And then the non-affiliated (online) dating agencies, carefully ticking the boxes of what she needs in a guy. She must make clear that non-matches need not apply. If money is no issue, she should consider a professional matchmaker (the classical solution before the internet era). These people are trained and, depending on the agency, have access to a quality selection of singles the world over. There may be a location – love trade-off: if the best guy is in, like, London UK, she may need to move there.
4. Tell The World. The previous two steps, and especially this one, are about cutting what Economists call ‘the information asymmetry’. Caitlin knows what she needs; the world – and especially Mr Right – do not. She can start by telling her friends (who tell their friends and so on). No worries about seeming desperate – talking about this shows confidence. If she has friends in the publishing industry, she may plot with them to find an excuse to portray her in a newspaper or newsletter or online community. Does she have a specific project she is leading, a volunteer activity or similar? Does she have an interesting story or experience to share? Have them narrate it, and portray her in the wake.
5. Give Yourself Time And Space To Decide. Once the phone starts ringing and the invitations coming, Caitlin needs to make sure the dates are meaningful and help her decide. Dinner or coffee are good, picnic too. As are moderately strenuous sports from hiking to tennis: they all give you time to talk. Cinema and theater do not – although they give you a theme, and if followed up by a meal, might make sense. Meeting in public until she feels safe is a no-brainer. Group activities are important to see how the date behaves around others, but getting too close too soon, e.g. involving family or very close friends, may influence Caitlin unduly. She needs to decide. And how best to do that will be the feature of another column…