Battling insecurity while dating – The Boston Globe


I have been dating someone for the past four months and it’s been good so far. However, within the past few days I’ve had these insecure thoughts and I’m not sure how to handle them. I’ve dated guys who have suddenly vanished without a trace/explanation (my last long-term relationship ended six years ago). I have a nagging fear that this new person may vanish suddenly as well. I keep these thoughts to myself as I don’t want to burden him with my struggles and/or make him feel that I am not worthy of dating. We have been spending a lot of time together recently (almost every night) and texting a few times during the day. I am not sure if these new insecure feelings are about my gut telling me something is a bit off, or just my paranoia about the possibility he could vanish.

It should be noted that this new man went out of town for the weekend recently to visit some friends. I was unsure about how much communication there’d be while he was away. He FaceTimed me three times, sent multiple texts, and called. I was pleasantly surprised.

But his behavior over the past few days has left me wondering. He hasn’t been as talkative as usual. He usually reaches out mid-morning or so to say hi — but it was after 2 p.m. and nothing, so I decided to reach out. I was conflicted because I didn’t want to appear desperate. He was fairly responsive. He didn’t want to get together that night as we usually do to grab dinner and watch a movie, and said he wasn’t feeling too good and wanted to sleep. Haven’t gotten the usual text today either. Is he slowly withdrawing? I don’t want to drive this guy away.

We do have fun and laugh a lot. We did recently go away for a few days and had a great time. I have to believe at almost 50 years old he wouldn’t be spending a lot of time with me if he didn’t want to. I have been introduced to some family members and some of his closest friends, and he has met mine. I am starting with a therapist to sort through my insecurity. But right now, should I feel insecure?


A. Look, I think a lot of people would tell you that if they were dating someone new and wonderful, and that person changed their communication style and started texting less, there would be big-time insecurity. Dating is stressful, even when the other person’s behavior is consistent. Meeting someone great means there’s something new to lose. It’s a lot to think about.

Stop punishing yourself for feeling a bit unsteady. The beginning of a good relationship often is uncomfortable because you’re trying to enjoy it but also asking, “Wait, is this something that might last?”

I’m glad you’re going to therapy to sort all of this out because it’ll help you figure out how your past affects your present, and how you can communicate your needs to someone new without asking for too much. Most likely, there is no way someone can sleep over every night, text all day, and FaceTime multiple times on a trip … forever. That’s a lot to keep up with, and there are bound to be some days with less. You can practice talking about that with your mental health professional. You can also come up with strategies for dealing with the discomfort — like staying busy with friends and hobbies, so you have other things to think about.

Please remember that this isn’t just about how he feels about you. You’re also evaluating him — deciding whether he might be a good partner. You might be the one who ends the relationship at some point.

Sometimes letter writers seem so focused on keeping someone around that I wonder if it distracts them from making their own decisions about their needs. If this guy starts being bad for you, you should want him gone.



Count me among the people who is happy to not be dating in this overreactive world where someone not responding to a text for a few hours is something to worry about. Phones have an off button, you know. So much of this unnecessary angst today is caused by an irrational expectation of immediate responses to frivolous electronic communications. Put the phone down, back away, and nobody gets hurt.


YOU should know there’s no guarantee about anything in life (OK, death and taxes). Instead of always preparing for the worst, work with a therapist on enjoying the present. Work on understanding that the world won’t end if this four-month relationship goes bad. If you don’t get these extreme insecurities under control, you’re correct, they’ll creep into your dating. One thing you definitely need to address for sure is the “worthy” statement. That made me sad when I read it. You’re worthy of finding love, we all are. Good luck.


I’m glad you’ve started therapy. If you’re waiting for this man to leave you, that’s not healthy — and these things have a way of becoming self-fulfilling prophecies. That was a lot of communication over the weekend when he was visiting friends. I wonder how much of this was done of his own volition or if he’s sensing you’re insecure and wanted to reassure you. That can be exhausting. As for his quietness, sometimes people want space and it has nothing to do with anyone else.


He is pulling away and that’s OK. Not every relationship is happily ever after. This isn’t about insecurities, it’s about life. You’re not going to be first choice for everyone. Accept that and make the most of what you’ve got. This guy is checking out.


Try looking more for patterns of behavior, rather than getting startled at a one-time change. It sounds like this guy is being pretty solicitous and responsive, so I don’t see a problem here.


Send your own relationship and dating questions to [email protected] or fill out this form. Catch new episodes of Meredith Goldstein’s “Love Letters” podcast at or wherever you listen to podcasts. Column and comments are edited and reprinted from

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