I feel that I’ve become a hopeless romantic who’ll never meet anyone with whom I can have a lasting relationship.

I’ve never dated and think that perhaps I’ve left it too late for someone of 38 years.

I seem to have focused mainly on my career and saving for a house.

And my shy persona seems to have kept me from making any headway toward dating.

I’ve tried all the apps and have gone on a couple of coffee dates but felt there was nothing there, so didn’t pursue it further.

Is there still hope? I’m eager to find that special one and settle down but maybe it’s too late? Any tips on what I can try next?

Forgot to Date

You’ve been very good at focussing on what you wanted previously – career, a house…..

Time to re-focus.

For someone who’s shy about using apps to meet with strangers only to find there’s “nothing there,” there’s another route: A professional matchmaker.

Yes, there’s a cost (find one you can afford). But there’s also the opportunity to have a person experienced in the process of assessing your qualities, personality, and interests, checking the signed-up “stock” of potential partners with whom there could be a match for you.

Also, a matchmaker knows what’s realistic in terms of hopes and dreams. At 38, you’ve done too little dating to realize there’s more to partnership than connection based on looks or charm.

With this approach, you’ll learn about a potential date’s education, job, previous relationships, general character, and any deal-breakers for you.

That’s a lot more than you gleaned from those coffee dates.

If you don’t find the matchmaker route appealing, try to put the same determination and steady progress that you applied to your other goals.

Try dating apps geared to specific factors, such as your background, religion, etc.

Review the meetup.com groups based on interests – music, a sport, restaurants, etc. – and join to widen your exposure to more people and dating possibilities.

(Even new women friends can help you meet new potential dates).

I’m a 24-year-old guy who met a woman on a dating app. We chatted easily.

We’d discovered we like the same kind of music, so agreed to meet at a club downtown.

She was what I expected from her photo – pretty, with a nice smile – and it seemed I looked as she’d expected. First test, we both passed.

That was all. Though we’d managed online, our conversation in person went stale after the first “hello.”

It reminded me of what my parents warned when I got my first phone as a teenager.

They said that if we weren’t thoughtful about it, my generation would become socially inept at conversation.

I don’t want to be that guy who settles for always communicating that way. How do I find someone like me who really wants to share thoughts in person?

Hello, Goodbye

You just learned that you’re not “that guy” on your short-lived last date.

While it’s generally wise to meet someone in person within a short time of meeting online, those early chats can reveal more than music preferences.

Some questions to ask, while making sure not to sound intrusive nor judgmental: What do you like to read? (Follow with, what are you reading currently?). Have you travelled anywhere interesting? What do you like best about your job (or dislike most)?

After a couple of chats like that, you should know if there’s any point in meeting.

FEEDBACK Regarding the woman who felt that her much less-affluent sister-in-law hated her (Feb. 8):

Reader – “Having experienced this situation within my own family, I believe the surest way to alienate her further would be to invite her to something like a movie, play, or concert and pay for it.

“Rather than feel a hand extended in friendship, she'll more likely feel a handout extended in charity. The source of the ill feeling is money.

“I suggest they find common ground on simpler things they can both afford and that set them on a level playing field – favourite books, Netflix binges, coffee/tea/cocktails, etc.

“Much to my regret, my own sisters, now approaching their 60's, have let this kind of imagined rivalry damage their relationships with one another.

“It was always about the money with them and they learned too late the lesson of loving and accepting people for who they are, not what they have.”