By luck, a dating site matched me up with a childhood friend (now both mid-40s). She's also never married, has no kids.

I have a manager’s job, she’s a high-earning professional ($500,000 annually), and owns rental properties. She's a very responsible, level-headed woman.
Last spring, I sent her flowers to work ($90). She raved over how beautiful they were and how everyone liked them.
When I started a new job, we shared a $350 dinner – she felt guilty and gave me $100.
And when her birthday came around, I bought her a gift which ruined our relationship.
We were in early stages of dating and intimacy, during which time she’d lost 20 pounds on a strict diet, in anticipation of a family wedding.

So I bought her a gift-card for $150 to get some nice yoga pants – her "go-to" casual wear. She's petite, so losing 20 pounds was a big change. She’d look amazing in them, I thought.
She was initially thrilled, happy, flattered. We spoke every day. Then her texts told a different story: The gift was too much for a friend. She went to the store and nothing fit. Could I please return the gift-card?

I was shocked and disappointed. Gift cards can't be returned.
I fear that she changed her mind about our relationship – it was early dating so somewhat like "friends with benefits" – we didn't discuss being exclusive, but I thought we were.
I'm heartbroken. I truly loved her. There was no ulterior motive. Truthfully, $150 is about two hours of work for me and I have no hope of impressing her or buying her affections because she's so much better off than I am.
I’ve apologized, repeatedly. I thought I was forgiven until just before Christmas when I took a business trip and said I had something (inexpensive) for her. She brought up the gift card again.

I’m heartbroken. I don't know how I could’ve known that this would cause a problem. Now I'm afraid that I'll make the same mistake with someone else. But I’ve lost my nerve for dating.

Blindsided

It does sound extraordinary that such a well-meant gift could destroy a budding relationship.

It seems unusual, too, that this connection which you thought was moving towards love, might’ve been, for her, just friends-with-benefits…. which translates to being a time-filler until The One comes along.

So, let’s look deeper at the details:

Money is a background issue here. She earns a lot more than you do, that’s not uncommon among couples that count their emotional bond as most important. Also, you were clearly generous on occasions.

Yet perhaps this last gift was a reality-check about disparate incomes that influenced her against having a future together.

Weight is another tricky issue. You admired her new, slimmer figure and rewarded her, but many women today seriously dislike having anyone else discuss their body image.

Or, an even more negative thought – she’d been dieting towards attending a wedding. Was there someone special she hoped to impress there?

Enough speculation from me and anguish from you. Speak up. Tell her that you truly loved her and had thought you were both dating in the hopes of a lasting relationship.

Ask her to honour that time together by helping you understand what the “gift card” symbolized to her – was it about financial differences? Or offensive in some way? Or, if she was just moving on and that was her excuse.

Once you know, you’ll handle this better.

I’ve been seeing this guy for a couple of months. He’s really nice and a gentleman, but we only get together during weekends. I sleep over at his place, we eat out, then watch a movie.

We only talk on Facebook, not by phone or text. I want and need more - call him, and hang out during weekdays too. But his full-time work is one hour away, so he might be tired or exhausted after.

Am I asking for too much? Or is he just not interested?

I Want More

This arrangement that would fit the label “friends with benefits” except for one missing factor: You’re not really close friends.

He’s not offering “more,” and that may not be because of you, but rather his disinterest in a close relationship with anyone.

Be “busy” next weekend. If he comes after you, be “busy” again soon. You’ll learn whether he’ll ever provide more.