You send that potential lover a Valentine to let them know you’re interested, and to see if they might be interested too. A true go-getter, Lisa May went about things in a more direct way. The single, 35-year-old Kiwi girl came home from London last year despite warnings from friends of Wellington’s ‘man-drought’ – often the reason they had not returned. Deciding to put their claims to the test, May challenged herself to ten first dates in January.

With the objective of meeting new people and maybe finding love, she opened a dating profile online and set her criteria for potential suitors. If they were 34-45 years old, single, looking for a relationship, living in Wellington and had ticked the ‘want children’ box, May was prepared to give them a shot. Despite the criteria, May’s first message was from a Southland train driver, reading, “Your a attractive women [sic]”.  Not a good sign for a self-confessed grammar Nazi.
But the messages kept rolling in. “I quickly realised I’d get more interest than I expected,” she says.
May received 53 messages, and those with a personalised reference to her profile (i.e. “I like that movie too”) got greater consideration than those copied-and-pasted. Acting on advice not to message for too long before meeting - “It builds up too much anticipation,” she says - May started dating.

#1: The Magician
“He did magic tricks for virtually the entire date. Oh, they were good magic tricks, it just made it difficult to converse.”
Verdict: “Another man told me a story about meeting a woman for a brunch date, and at 11am she fell over his table drunk. He was surrounded by families and his date was on the floor with her knickers showing. The Magician was a good introduction to first date experiences for me.”

# 2: The Mature Student
“He was one year younger than me, but it felt like he was twenty years younger. We both had a drink, and then when the bill came he put the exact change for his beer down on the tray. It’s such a student thing to do. I’d prefer ‘I’ll get this round, you get the next’.”
Verdict: “We had great philosophical conversations about life, but we were on different planets.”

# 3: The Wheelchair Athlete
Competitor in marathons and wheelchair rugby, “He had the nicest arms I’ve ever seen,” says May. “We talked for three hours and it felt like half an hour, it was really inspirational.”
He was also the only date who insisted on paying for May’s lunch.
Verdict: “He was such a great guy, but I feel too selfish to go into a long term relationship with someone with a disability.”
#4: “Stavros”
“He had an open white shirt and a gold chain. I should have kept walking.”
“He spent the whole date namedropping people I didn’t know, by their first names, and talking about how he wore Armani suits. No one who wears Armani suits talks about how they wear Armani suits.”
May was happy to pay for herself on all dates, which is a good thing.
“He talked about how he’d paid off his mortgage, and then didn’t offer to pay for my glass of wine.”
Verdict: “He was arrogant but without confidence, which is a really hard thing to pull off.”

# 5 Mr. Chilled Out
“He was so chilled out that sometimes he’d be half way through a sentence and he’d forget what he was saying. He’d either had too many drugs earlier in his life, or earlier that day.
“We talked about starting a hippie commune.”
Verdict: Not long-term relationship material, but if May starts a hippie commune, Mr. Chilled Out is definitely invited to join.

# 6: The Ex-Rugby Player
“He asked a couple of really inappropriate questions, like if I’d ever had a threesome or been with another woman. To be fair the conversation was already in the gutter, but are they first date questions?”
Verdict: We were just on different wavelengths.

# 7: Nice Mountain Biking Guy
“He was really, really nice. He was too nice.”
“And there was a first date faux pas. It came up in the conversation that he was colourblind, and he said, ‘but it’s carried on the female gene so our kids won’t be colourblind unless you are’. At which point he realised what he’d said and started backtracking, ‘oh, if we have kids’...”
“Don’t use ‘our’ and ‘kids’ in the same sentence on a first date,” May laughs.
Verdict: “He’ll be really nice for someone, but not for me.”

Favourite Date Number Eight
“We met for lunch at Lido, and we got chatting straight away – to the point where the waitress had to come back four times to get our order. There was great conversation, and chemistry which was missing in the other dates.”
Verdict: “He was the only one I genuinely hoped I would see again. He’d mentioned a second date, and that night we exchanged a few texts which was nice. We arranged to meet each other again, but ended up seeing each other before that…”

# 9: Socially Challenged
“He had an iPhone, and he pulled up my dating profile and asked questions from it. He started going through the pictures on my profile, holding his iPhone up next to my face to see if I’d fairly represented myself. Then he slipped into conversation that his family had a history of mental illness, and before I could say anything about it he got really defensive.”
Verdict: “He asked if we could catch up for dinner on Thursday, but I said I couldn’t because I was speed dating. Later that day he got in touch again saying ‘I found the speed dating and I’ve signed up, that can be our second date’.”
Ends up, he didn’t make it past the waiting list.
“It ended well. I felt for a moment I might have a stalker on my hands.”

# 10: 60s/70s Guy
“He runs a retro fashion and accessory store, which sounds very cool. He’s a very interesting guy.”
The verdict: “There’s not too much to say, it just felt like we came from different eras.”
By January 20, May had successfully completed her mission.
In fact, she’d technically dated 20 men in 20 days, as she spent seven minutes each with ten men at speed dating. “There was one guy who came in with a bag of single stemmed roses, and gave one to each woman. It’s weird enough getting a rose on your first date, it’s even weirder when you watch him go round the room giving roses to all the other women.”
The only man she dated more than once was Favourite Date Number Eight, who coincidently was also one of the speed daters.
“It was a little awkward at first, but we laughed and agreed that the Wellington dating pool was small, and it could just be our second date.
“After speed dating he offered to drive me home, and finally after ten normal dates and ten speed dates I had my first date kiss. It was exceptional.”
May and Favourite Date Number Eight have now had five dates, and she’s optimistic, whatever the outcome.
 “Einstein said ‘Setting an example is not the main means of influencing another, it is the only means’, and I absolutely believe that. If, by doing this, I can inspire others to put themselves out there, it’s all I can ask for.”
May has now challenged herself to ‘6 things I’ve never done in February’; last week she stripped off the suit she wears for her management job on The Terrace and jumped into the harbour in her underwear. Next up: Life drawing, kickboxing and belly dancing.
“I’ll keep you posted,” she says.