Ask Amy: Single man searches for the right match

Dear Amy: I’ve been single since high school (I’m currently 27 years old).

Dating has never been exactly a priority of mine, but I do want a romantic relationship in my life.

I’ve been on several dating apps for the past few years, and have finally matched with a real, genuine human (as a man, the odds of that happening are disproportionately slim).

We’ve been talking for a while, but I’m the one who’s been carrying the conversation.

I’m asking all the questions like, “What do you like to do in your free time?” or “How has your day been?”

She replies with very short answers that have made it increasingly difficult for me to proceed.

I know so much about her, yet she hasn’t exactly shown much interest in me.

I have mentioned a few things about myself organically, but she doesn’t respond very intensely to anything I offer.

There is the possibility that she would communicate better in person, but at this point I’m reluctant to get to an in-person meeting.

Is it wrong to make that assumption from our solely remote interactions?

Should I keep taking the initiative, though it’s like pulling teeth, or should I let her know that I’m not feeling a connection and cut the loose ties before anything gets too serious?

– Looking

Dear Looking: It’s hard to imagine things getting “too serious,” with this match, given your completely reasonable desire and expectation to have a relationship with someone who expresses an interest in you.

So yes, it is time to move on. You can reply, “I’m not sensing a connection here, but I wish you all the best in your search for a relationship.”

It’s not necessary to provide any further explanation, unless she asks for one.

You say you’ve been at this for some time without success, and so you should also take this opportunity to review the venues you are using to try to find a match, and to refresh your own technique.

Review (or have a friend) review your photos and your dating profile. Choose a variety of flattering but realistic photos of you in different contexts. Make eye contact with the camera. Spiff up your profile and narrative. Focus on dating apps that have a larger number of people in your geographical area.

I’m also wondering if you might have better luck finding real, genuine people in real life. You know – in person?

One way to meet new people is to actually meet people. This is done by renewing/reviving your IRL friendships, joining organizations aligning with your interests, getting out there, and greeting people with eye contact and a smile at the coffee shop.

If you are 27 now, I’m assuming that your 10th high school reunion is coming up. This is a great time and opportunity to connect with people you haven’t seen in a long time. Find your class reunion’s Facebook page and make plans to attend.

Dear Amy: I have a work-related question.

Every year my boss goes over my evaluation, and the evaluation is always positive. There is generally a small pay raise awarded to me at that time.

I respond by saying thank you.

But then my boss goes on to say, "I’ve refused my pay raise this year so you all can have raises."

This has happened at least twice in the past four years.

I’m always at a loss for how to respond to that. It’s so awkward. Should I say, “Thank you”?

– Wondering Employee

Dear Employee: It is unprofessional for your boss to bring up others’ compensation (even their own) during your evaluation and salary discussion.

This person obviously wants you to feel (and express) gratitude for their stated sacrifice. You could respond by saying, “Thank you,” “I’m not sure how to respond,” “OK …,” or, “I’m sorry it has come to that.”

Dear Amy: I heartily disagree with your response to "Had It,” whose husband traveled to celebrate his brother’s birthday instead of his wife’s birthday.

Contact a lawyer? REALLY? It’s just a birthday.

Yes, I get it. Her husband seems to be choosing his brother over his wife, but it seems to me this wife is really searching for a reason to be mad.

My guess is that her husband and the daughters planned this "in secret" because they didn’t want to hear her whining about it.

You just fed her ego. It’s time she puts others’ feelings first.

– No Whiners

Dear No Whiners: “Had It” seemed to believe that this was the last straw.

(You can email Amy Dickinson at askamy@amydickinson.com or send a letter to Ask Amy, P.O. Box 194, Freeville, NY 13068. You can also follow her on Twitter @askingamy or Facebook.)

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