Sent a sext and overreacted

This letter writer shared a sext in her letter, but we can't have it on Boston.com, so you'll have to use your imagination. Please keep the comments section clean. I welcome all euphemisms. (The sext had nothing to do with grilled cheese.)

Also reminding everyone about Love Letters night with Boston Ballet.

Hi Meredith,

Longtime reader. I hope you can help. I broke up with my longtime boyfriend a little more than two years ago. I had a great year of being single and hanging out with friends after we broke up, and then I moved to Boston from the West Coast to start fresh with a new job and new surroundings. I've been online dating off and on (sometimes I get a little overwhelmed or discouraged so I get offline in order to refocus). I would say I have a healthy amount of self-confidence and am fairly mature.

About two weeks ago, I met this guy on Match who is new to Boston the way I was a year ago. We'd been messaging/texting for about two weeks, so I invited him to an impromptu hangout session with friends. We had a great time and I really liked him. I'm a 33-year-old ENFP, and he's a 32-year-old INTP, in case that helps. The next day, we stuck to our original first-date plan of visiting the ICA and having a late brunch. We were affectionate, but not in a vulgar way. It felt really nice. Anyway, we had a really great time again and had great chemistry, so naturally I caved when he put the moves on me, and we had sex. Three times. In one afternoon. I'm pretty comfortable with my sexuality and I enjoy having sex, so when I feel comfortable enough to have sex with someone, I just do, no regrets, and definitely none of that "Is it too soon?" mental anguish.

The problem is that later that night after I got home, I saw he was "ONLINE NOW!" on Match. Match should get rid of this function on its website to spare the users of the sheer insanity it brings out in them, but whatever, it is what it is. Paranoia overwhelmed me. How could he be "ONLINE NOW!" already? (Never mind the fact that I was too, just to see if he was online.) We had talked about how he wanted to explore Boston with me and get to know me better and put the kibosh on Match so he could focus on me.

The next day, I sent him a sexy text (which I never do, but we had such a good romp in the sack that I didn't think anything of it), and he responded that he had a headache and was starting to get sick but that he'd feel better the next day and see me as planned (dinner). I don't know why, but I just emotionally snapped. I literally thought, "How does he know he'll feel better by tomorrow, especially if he's getting sick?!" I uninvited him to dinner the following night and then sent a snappy text back. I think I felt rejected that I had put myself out there and sent a sexy text message but got such a robotic, non-emotional/non-sexual response, and was all of a sudden blind to the good things I liked about him. And ... in his defense, my text read, "[SEXY TEXT HERE]" which he probably interpreted to mean I wanted to see him that night, which actually is not what I meant since I knew I'd be seeing him the next night. My perspective is that he came on really strong, really quick (he talked about me helping him shop for Boston winter clothes, helping him with furniture shopping since in my profile I mentioned interior design is a hobby of mine, exploring Boston together, etc.). I allowed it and I slept with him. But the second I came on strong with my emotional snafu, like one day later(!), I was frozen out. I called him the next morning (I was surprised he actually picked up the phone) and tried to explain, but he said it was too much for him. Poor guy. He ended the call with "I'll call you later" but obviously hasn't. And I haven't contacted him again because I'm just not that desperate.

However, I've thought about this guy every day since, and I regret my overreaction. Would it be ridiculous for me to reach out to him again? I've read so much about dating, and I buy into "he's just not that into you" for when a guy does not contact me. But is it over? If so, fine, I concede and I've learned my lesson (again). If I do reach out, how can I do so in a way that he would hopefully respond to? Please help.

— Here We Go Again


Let this one go, my friend. He told you this was too much for him, so that's that. I won't scold you for having sex with him on the second date — I think it's great that you like sex and that you have it when you want it. But ... you have to be honest with yourself about what you can handle. If you're the kind of person who'll freak out and check Match all afternoon after having sex with someone new, maybe it's worth waiting until you feel comfortable talking about intentions. Or maybe you can set some rules for yourself about when and how often you're allowed to go online to check the activity of your potential suitors.

You said it best — you learned a good lesson here. Actually, you learned five good lessons. 1) No matter what happens on a second date, it's still just a second date. 2) Not every sext gets a sexy response, and that's OK. 3) Sometimes people feel sick but can guess that they'll probably feel better the next day. It happens. 4) If you feel the urge to send an angry text to some guy you barely know, call a friend and talk about it. Get some perspective before you hit send. 5) If you're on a second date and a guy asks you to pick out his winter clothes and decorate his apartment, nod and smile but don't take it too seriously.

Please forgive yourself, laugh this one off, and go on some more dates. Let this man disappear.

— Meredith

Readers? Is she allowed to reach out? Any other lessons learned? If she reaches out, what should she say?