Q:

There’s this person I really like. We met on a dating app and things are going well, but any attempt to take things further, a first date, some light flirting, is met with anxiety. Cancelling a date we’ve planned and confirmed, not replying to flirty texts until I make the move to ask what’s wrong and what I can do. I’m trying to let them set the pace, ask them questions about how they’re feeling, trying to feel out clear boundaries, they’ve even assured me they’re still interested, but I feel shut out, blocked emotionally. Is there anything I can do to support them trusting me more? Maybe being less nervous of dating in general? I wouldn’t want their fear to get in the way of what feels like a genuine connection.

A:

I was once in a very similar situation when single in my early twenties. I really hit it off with a girl I met on Tinder and felt like we had a genuine connection. We were flirty and funny over the app. Multiple times, we made plans to go on a date IRL. Multiple times, she bailed at the last minute or even intermittently ghosted. Every time, she’d re-emerge like nothing had really happened. Sure, she’d apologize, but the apology was usually vague and short and didn’t invite much conversation. Then the cycle would repeat. I was lightly frustrated, but I contributed to the pattern by never really asking directly about why she kept bailing. I’d ask how she was doing, how she was feeling, and if she wanted to keep talking (to which, she always enthusiastically replied in the affirmative). But I never asked: Hey, is there a reason you’re uncomfortable taking the next step?

She was certainly aware of her behavior. In fact, she became so anxious about having cancelled on me so many times that she eventually sent me a video of herself talking because she was worried I might think she was catfishing me since we’d never met or communicated over video. TBH, the thought had never even crossed my mind! I had dealt with her unpredictability by pursuing other folks on the app, even though there was a part of me that always longed to hear from her. (Sometimes, I wonder if her withholding behavior contributed to how invested I felt in her — not a great dynamic, to be sure!) Shortly after she sent that video, she opened up. She said she realized she wasn’t ready to date, even though she really thought she was. She liked talking to me, but every time things started to feel more “real,” she got scared. She was just off of a recent breakup, and even though she wanted to be ready to date again, she wasn’t. And her body/brain was telling her that every time she tried to make concrete plans with me, but instead of communicating it, she just bailed. Probably because that felt like the easier thing to do.

I don’t say all this to suggest that the person you’re talking to is going through the exact same thing or that they are not ready to date. I’m just using my own example as a way to demonstrate that it’s really difficult to know what’s going on with another person. In your case, it sounds like you’ve been more communicative than I was, giving them ample opportunity to open up or discuss their anxieties. If you haven’t yet, maybe explicitly asking: Is there a reason you tend to cancel dates/plans after we confirm? Make it clear you aren’t mad or judging their behavior but just genuinely interested in hearing their perspective. If they don’t want to share though, that’s also their choice, but it means you can make your own choice. You don’t have to keep talking to someone who isn’t able to match what you want and give in terms of intimacy and boundaries.

What’s hard about dating apps is that it’s easy to strike up an instant connection in terms of chemistry, rapport, etc. That can make it feel like there’s automatic intimacy and familiarity between two people, even when you’re in the beginning or casual stages of dating. It’s sometimes easier to open up over an app than it is in person. It’s not that it’s fake intimacy; it’s just different. It sounds like this person is perhaps more comfortable in that space but still have emotional walls up even there. I think a few different things could be happening here. It could be similar to my situation and this person isn’t really ready to date seriously but is on the apps to try to convince themselves they are. It could just be that this person is indeed just anxious and fearful of dating in general and takes more time to open up and commit. It could be that this person just is generally emotionally closed off in a lot of their relationships. And if that’s not going to work for you, then you can decide to move on to someone who’s going to be a better fit.

The only thing you can really do in terms of offering support is asking them what they need from you to feel comfortable. Any questions about how they’re feeling should be direct and explicit. Not just “how are you feeling” but “how are you feeling about our upcoming date” for example. Hopefully they will take the opportunity to be honest with you. But I do think it’s important to understand that sometimes people get on dating apps before they’re actually ready to date, because it feels like a low risk environment to do that in. It’s not fair to you as someone who is genuinely looking for connection and someone to date, but I do think it’s just the reality sometimes. I hope you’re able to find someone to have an open and intimate connection with — whether it’s this person or someone else.

You can chime in with your advice in the comments and submit your own questions any time.

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