I give off a ‘non-dating’ vibe

Dear Meredith,

I'm 31, professionally successful, have good friends, and am involved in some dynamic, rewarding hobbies. By all accounts, dating should not be as hard for me as it has been, but it is. I was a late bloomer – didn't date in high school and had my first kiss at age 19 – and I feel like I've been playing catch-up ever since. The more I fall behind, the harder it feels to catch up to where I feel I should be in terms of overall dating/relationship experience at my age. I've had a couple of relationships that lasted less than a year that taught me a lot, and some first and second dates (mostly online/app originated) that go nowhere, but otherwise dating just feels like the ultimate white whale that persistently eludes me. I fear that at this point in my life, I somehow unconsciously give off a "non-dating" vibe or something that I can't figure out, and I'm afraid that I'm never going to have the kind of fulfilling, monogamous relationship that I want as part of my life.

This fear ratcheted up recently when I met someone at my new job who really draws my attention. He's smart, seems very kind, and I would really like to get to know him better, but I think he is a bit shy. We sometimes exchange emails that turn into friendly, joking banter that will go on for a few rounds and then one of us drops it. I feel particularly nervous as the new person in the office – dating someone from work has always been something I've preferred to avoid. Plus, I'm terrified that he's just being nice, and that if I tried to take it beyond these safe interactions, he would have to awkwardly tell me he's not interested and I would feel humiliated. My limited experience feels very, well, limiting in this instance. I don't want to miss out on a good thing, but I also feel completely out of my depth here. How do I push past my own insecurities? And how do I figure out if these email flirtations are for real on his end or not?

- Inexperienced and looking for love

The thing about experience is that it doesn't necessarily give you any answers. People who've had a string of serious relationships might not be any better at decoding flirtation. In fact, people who've spent time much of their adult lives with partners and significant others often feel like they have trouble knowing how to be single. Everyone's inexperienced at something.

There are some people who've done a lot of dating and have trained themselves to be less afraid of rejection. They know that if someone isn't interested, it's not the end of the world or an important statement about their worth.

Maybe those date-a-lot people are better at giving off a dating vibe, in general. They might be breezier about saying what they want – that they're looking for companionship – and asking for it. You can be that kind of person. Once you say something like, "Hey, I'd love to get together after work," and the world doesn't end, you'll feel empowered to try again.

Dating at work can be tricky, but making friends in the office is a good place to start. You can ask this man to join you out after work with others. Group outings are a great way to connect outside of cubicles, and then, depending on the vibe of the night, you can proceed from there.

– Meredith

Readers? Like Wednesday's letter, this one is about feeling left behind when it comes to dating. In both cases, the letter writers say they have had relationships and lots of dates ... so they don't seem left behind to me? Does anyone feel like they're having the "right" experiences? Help.