Battling Insecurity While Dating

What’s been on your mind about your relationship life? What’s stressing you out? Send a question about it to [email protected] or fill out this form.


Can you offer some advice on how to battle insecurity and trust issues? I have had long-term relationships that ended very badly resulting in these insecurities. I am working through them as best as I can, however, I can’t seem to stop my brain from overdrive when they creep in.

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 unsure how exactly to handle them. My last long-term relationship ended six years ago. I have dated guys that suddenly vanish without a trace/explanation. I have a nagging fear that this 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 he went out of town for the weekend recently to visit some friends. I was unsure about how much communication there would be while he was there. He FaceTimed me three times, multiple texts throughout the time, and a phone call. 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?

– paranoid in private


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. Who wouldn’t feel that way? Even if his communication was exactly as it has been, dating someone great is stressful – because there’s something to lose.

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

That said, 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 any person can sleep over every night, text all day, and FaceTime multiple times on a trip. That’s a lot to keep up with, and there are bound to be some days with less. You can practice talking about that in therapy. You can also come up with strategies for dealing, which might include staying busy with a lot of other things to think about.

Please remember that this isn’t just about you trying to keep him around. 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 interested that I wonder if it distracts them from making their own decisions about the person in front of them. If this guy starts being bad for you, you should want him gone.

– Meredith

Readers? Tips for battling insecurity during this phase of a relationship? Is it worth bringing up with him? Too soon?

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