Ask Ellie: Woman of man’s dreams has a boyfriend already

Q: Coming from a small town, I’m a guy who holds gentlemanly charms and qualities close. But it catches people off guard and uncomfortable when I enter the dating scene.

I finally caught the attention of someone earlier this year, or so I thought. I’d frequented a family-run restaurant for a year and often made small talk, since she was the only one who worked there anywhere close to my age, 33.

Though shy and timid, I finally got the courage to give her my number and tell her how much I liked her sense of humour.

Eventually, I got a friend request and a Facebook message from her.

We hit it off; I asked her out once and thought I’d finally found my match. But during that date, she referred to her boyfriend.

For some reason that didn’t stop me. When I took her home, she gave me a rather meaningful hug goodnight. We keep seeing each other as friends, at her work, or hanging out elsewhere.

We’ve planned a trip together later this year since she hasn’t travelled in years and I want to share my travels with someone.

I don’t know where to move next. I’ve never had a connection like this before.

She makes me incredibly happy, I get butterflies whenever I see her, she sees me for who I am, and I haven’t felt depressed, insecure, or anxious since I’ve gotten to know her. I could see something working between us long-term.

What should I do? I want to push for something more, but I can’t tell her to choose me over her boyfriend of four years.

And I don’t want to risk jeopardizing the friendship.

Uncharted Territory A: Whenever there are feelings involved, there are risks. Avoid them, and you don’t get what you want.

Take a step forward, and you have a chance.

Start the conversation: Is she committed long-term to this boyfriend?

If so, how does she define your friendship, and what has she told him about you?

You don’t want her sneaking out with you, if that’s happening, because eventually he’ll find out and there’ll be drama you won’t like. And the friendship will end. Or, she’s told him you’re “harmless,” or whatever, when the truth is you’re a man who wants to have a romantic relationship with her.

Once you start talking to her about having feelings but also caring about the friendship, you’ll have more of a chance than what you have now.

FEEDBACK Regarding dealing with the past bad history of a dying relative: (June 19):

Reader — My one sister allied my mother against another sister and me, over a family situation.

We struggled, despite buried hurt and anger at both Mom and that sister, to stay connected to our mother during her lengthy illness.

A month before Mom died, I was at the hospital visiting her and all the anger I felt just vanished.

Suddenly, it didn't matter what had happened. A wave of compassion for Mom flooded over me. I realized she would die soon.

The letter-writer shouldn’t confront his dying relatives as they’re already coping with enough.

If he visits briefly (with a supportive person) he’ll see their suffering from illnesses first-hand.

As for the funerals, take the high road and go. He’ll feel better about himself as a person.

Again, take a supportive person along and only stay as long as you’re comfortable.

Then, with a really close friend or counsellor, talk through the whole situation.

TIP OF THE DAY Don’t hide romantic feelings for a friend. No risk, no chance.

Read Ellie Monday to Saturday. Email ellie@thestar.ca.