How Can Someone Return to Dating After Eight Years Away?

A reader who has not been on a date in eight years is preparing to re-enter the dating world in 2027, but says anxiety, financial insecurity as a student writer, and life as an expat in Singapore are making the prospect feel overwhelming. In response, advice columnist Annalisa Barbieri, working with UK Council for Psychotherapy (UKCP) accredited psychotherapist Hannah Jackson-McCamley, suggests the reader examine whether they genuinely want to date now or simply feel they ought to, and recommends starting with real-world connections rather than dating apps.

What is the reader's situation?

The reader describes wanting to love and care for someone, and longs for a partner who is both supportive and funny, but is unsure whether expressing this directly to a potential partner, or including it in a dating profile, would be too much. Having sworn off relationships until their anxiety was permanently resolved, the reader is an expat currently based in Singapore who is still building a social circle and feels uneasy around people they do not know. They also describe embarrassment about being a student and a writer without significant income, in a context where, they feel, many people around them prioritise career achievement.

Why does the reader describe dating as a "storm"?

Barbieri and Jackson-McCamley both noted that the reader's choice of words, calling dating a "storm" and asking how to stay brave when "lightning strikes", was striking. Barbieri questions why restarting dating carries so much weight for the reader, pointing to the pattern of holding off until conditions feel exactly right and setting a future date, such as "next year", to begin. She suggests this kind of postponement often happens when someone does not yet feel ready but believes they should proceed regardless, and argues that dating tends to go best when a person already feels settled in themselves, so a relationship adds to their life rather than filling a gap in it.

Jackson-McCamley wondered whether the reader's

relational experiences, dating or otherwise, might associate relationships with being tumultuous and something one has to prepare for or defend against

Barbieri notes that early experiences can shape how people anticipate relationships will unfold later in life.

Jackson-McCamley also reflected on the reader's stated wish to love and support a partner, saying:

beautiful you want to be so generous with your love … but I wonder if being a caring person is part of your script and perhaps redolent of the role you take in relationships? It's also great that you are able to articulate what you want from a partner and are considering making it clear from the start. However, not everyone may be used to such clarity or be looking for a life partner.

Barbieri points out that because the reader has deliberately avoided dating for years, they may take the process more seriously than people they meet, who have likely continued dating throughout that time and may initially approach it more casually. She stresses that this difference in intensity is not a problem in itself, and that both parties are entitled to their own pace and expectations.

How does anxiety factor into dating again?

Jackson-McCamley addresses the reader's reference to fixing their anxiety permanently before dating, explaining that anxiety is

a totally normal response to a perceived stress or danger, so it isn't something you need to permanently fix. But I'd be keen to explore your experience of anxiety in relation to dating – and beyond. I want you to feel reassured that no one is 'fixed', we are all works-in-progress.

Because the reader did not share much else about their broader circumstances, Barbieri and Jackson-McCamley say they were left wondering what else might be going on in the reader's life. Jackson-McCamley offers reassurance around the difficulty of building new friendships in an unfamiliar setting:

Give yourself grace

she says,

for trying to make friends and confronting your nerves around new people. I wonder if this is the first time you've felt different or like an outsider?

She encourages the reader not to undervalue what they can offer a partner

beyond traditional accoutrements of status: money, job title, etc

noting that the reader's own stated priorities, a supportive and funny life partner, are not about material status, and that other people's priorities may not be either.

Barbieri concludes that falling in love always carries some risk, whether real or imagined, but observes that the reader already interacts with people daily through student life, which she considers an ideal setting for meeting others, whether for friendship or romance. She suggests that rather than turning straight to dating apps, a gentler approach rooted in forming friendships first, and allowing romantic connections to develop naturally from there, might suit the reader better.

What does Singapore's dating landscape look like right now?

Beyond the reader's personal circumstances, recent survey data offers wider context on dating in Singapore, where the reader is currently based. According to a Straits Times survey published in April 2026, nearly half of around 1,000 respondents aged 18 to 35, covering both single people and those in unmarried relationships, described the local dating scene as "bleak", citing limited opportunities to meet people, high living costs, and frustration with dating apps. A follow-up Straits Times report from June 2026 examined how a growing preoccupation with spotting "red flags" and "icks" in potential partners has become a defining feature of contemporary dating culture in the country.

These findings echo some of the reader's own concerns about financial pressure and social difficulty as an expat, though the reader's worries are also shaped by their personal history and current life stage rather than local dating trends alone.

Historical background: the risks of dating apps

Separately from the reader's specific situation, broader research has raised concerns about the psychological effects of dating apps. A 2025 report found that compulsive use of dating apps has been linked to poorer mental health outcomes, including heightened anxiety and loneliness, which may lend some support to Barbieri's suggestion that the reader consider a more real-world, less app-dependent route back into dating.

Separately, guidance published in 2026 by a Singapore-based counselling service states that dating-related anxiety can be managed with professional counselling support, offering a potential practical avenue for readers in a similar position to explore alongside the advice given in this column.

What happens next?

Readers in Singapore looking for structured, in-person support around dating and relationships have a couple of scheduled options in the coming months. According to a February 2026 partnership announcement, Safe Space and Coffee Meets Bagel are set to roll out a Relationship Wellness Workshop Series during 2026, aimed at helping participants build healthier and more emotionally resilient relationships. Separately, So You Socials has scheduled an offline "conscious dating" social event for people in their 30s and 40s on 27 June 2026 at 7:30pm, offering an alternative to app-based dating that aligns with Barbieri's suggestion of a softer, real-world approach.

Key Facts

• The reader has not dated in eight years and plans to resume dating next year while living as an expat student in Singapore.
• Psychotherapist Hannah Jackson-McCamley says anxiety is a normal response to stress rather than something that needs permanent fixing before dating can resume.
• A Straits Times survey published in April 2026 found nearly half of 1,000 respondents aged 18 to 35 described Singapore's dating scene as "bleak".
• Safe Space and Coffee Meets Bagel plan to launch a Relationship Wellness Workshop Series during 2026.
• So You Socials has an offline dating social for people in their 30s and 40s scheduled for 27 June 2026.