We didn’t kiss on the first date, but during our second date, he kissed me by a secluded part of the lake and we kissed occasionally throughout the date, pretty tastefully, I guess — no heavy PDA. We held hands. It ended up being an 8 date and I enjoyed it. At the end when he walked me to my car, we had, I’d say, a heavier make-out session, standing up. Then, he asked me if I wanted to go back to his place. I said I didn’t think it was a good idea. He took it fine and we said our good nights.
I’m just thrown. Was that a harmless question? Is this normal (I’ve never had a “relationship” last longer than 5-6 dates, so I’m inexperienced)? Did I come across like I would want to have sex with him on the second date (slash “go over to his place”)? You wouldn’t be able to answer that, I know. Not that having sex on the second date is bad for people, if they want it, but it’s not me. There were possible red flags on the date, like he seemed to remember details that could fit other girls, like the school I went to or how much of a TV show I watched, but I brushed it off, because well, that stuff happens during online dating. While we were waiting for a movie, he pulled out the New York Times 36 Questions thing, but it was an app so he clearly had already downloaded it before. I thought it was kind of cute, and also a little “hmm,” but I brushed it off too.
Anyway, I haven’t decided if I want to see him again if he texts me. I don’t plan on reaching out to him although it’s disappointing since I had fun today. And I guess there won’t be “closure” if neither of us reaches out to the other, but maybe a mutual fade is best in this situation. I don’t know if I really want to go out with him and what would happen on the third date. Maybe his question of going back to his place was just in the moment. I don’t know.
UPDATE: Just to let you know: he did text me yesterday saying he enjoyed the date and he didn’t bring anything up about what I wrote to you. I did reply to him and we’ve texted a bit since. That’s the thing, he seems so normal and nice that what he said confused me. — Too Much to Think about after a Second Date
Well, color me confused. You are both in your late 20s, on a second date, enjoying some making out, which you seemingly are actively engaging in and not stopping, and when the guy asks if you’d like to go back to his place, you think that’s a red flag? For what? That a guy might be interested in spending some more time with you? In private? Being intimate? I mean… that’s normal. I guess you don’t realize that’s normal, but it is. And not only is it normal, but it’s also “nice.” Like, nice people occasionally enjoy intimacy with other nice people, and sometimes even on a second date. I don’t mean to shock you, but sometimes it even happens on a first date. And while you say that “having sex on a second date isn’t bad for people,” implying that you don’t judge it, I think you absolutely do judge it. You’re certainly judging this guy who — not for nothing — didn’t pressure you, didn’t kiss you on the first date, and immediately dropped the topic when you declined his invitation to go back to his place (which doesn’t necessarily mean he was only interested in having sex with you. Maybe he just wanted to continue making out, but doing so in a more private and comfortable locale. Maybe he wanted to show you his record collection. Maybe he just wanted to go over more of the 36 questions with you).
And I think it’s weird that his remembering details about you is also a red flag for you. I get that you’re inexperienced — clearly — but a guy remembering where you went to school and what TV shows you like is only showing sincere interest in you. In fact, this sincere interest in you as a person — your personal history and your interests — directly refutes your implication that he’s only interested in sex or somehow not respecting you. He’s not only showing interest in getting to know you — that 36 questions thing, as silly as you may find it, is another example — but he is also showing interest in you physically, AND respecting your personal boundaries, AND following up your dates by reaching out and continuing conversing with you. SO, WHAT’S THE PROBLEM HERE? I don’t get it. Are you just looking for something to not like? Are you afraid of what will happen if this goes past the sixth date? Are you afraid of being in a relationship, being intimate with someone? At 28, these are serious issues, and you may want to consider talking to a therapist about your concerns. You’re hung up on what’s normal and what isn’t, but the only person in this scenario who is acting in an atypical way is you.
I can’t help but wonder if he is trying to overcompensate and heal his hurt by putting so much effort into dates with me. When we are not together, we rarely talk unless we send a few short texts here or there to plan to see each other, he never flirts with me through the texts, and sometimes, although he will message me, he will not respond to my replies. It makes me question if he is really interested in me. We have had sex twice now and both times he lost his erection about halfway through. He said that this was a recent problem and it was super embarrassing, so, of course, I told him don’t worry about it, but I could not help but feel like it’s because he is not attracted to me or is thinking of his ex.
He told me as he was lying there that he has anxiety and gets nervous around me because he likes me but was feeling like I was too good to be true. I guess my point is I am not sure how literally to take the things he says and all the sweet gestures when he doesn’t flirt or seem sexually attracted to me. The last guy I dated ended up completely rejecting me and I am so fearful of it happening again this time around, especially because I have already developed feelings for him. How should I interpret the things he says? — Not Too Good To Be True
So, the sinking feeling you have that he is not over his ex is based entirely on his lack of flirting with you in texts and his erectile issues the two times you tried to have sex? What do either of these things have to do with his ex? Nothing! They literally have nothing to do with his ex at all. The lack of flirting in texts could 100% be the way he is — not everyone flirt-texts. You say he’s using texts to plan dates with you, which is… normal. That shows normal interest in you. Not everyone uses texts to chitchat throughout the day and stay in touch. Not everyone has time for that.
I just don’t understand how, on one hand, you’re concerned that he’s putting so much effort into dates with you because you think that’s overcompensating for something and you can’t truly believe he’d be that interested in you, and then, on the other hand, you’re using his lack of flirty texts to support that he’s not really interested in you. Well, which is it? He’s either showing too much interest in you to be believable, or not enough. Pick a lane.
Like the first LW, you sound like you’re just looking for reasons to not like/trust this guy. You have baggage from a previous relationship and are projecting it onto this guy. Not every guy is going to be the last guy you dated who “completely rejected” you, and if you’re “so fearful of that happening again,” to the point that you can’t trust a guy’s intention when he puts efforts into dates with you, you aren’t ready to be dating again.
Here’s the thing: There’s a good chance you’re going to be hurt again. That just happens in dating. Even when you find your right match, you can still get hurt, because we’re all human and we all say and do things that hurt the people we love. And until you meet the right match, you are probably going to date guys who are the wrong match for you. Sometimes you may like them and they don’t like you back. Or they like you and you don’t like them back. Or you both like each other a lot and enjoy spending time together but realize you have different values or different goals or are looking for different things or simply don’t have enough in common or enough of a shared communication style to sustain a serious relationship. And that can hurt. It can hurt more that unreciprocated feelings because it’s so frustrating to get close to finding what you’re looking for only to have it be not quite right. All of these things can create semblances of a broken heart. You need to be prepared to handle a broken heart when you’re dating, just like you need to be prepared for a flood if you live in the panhandle of Florida during hurricane season. Broken hearts come with the dating territory. It’s always a risk when you allow yourself to like someone and pursue a relationship with him. But with risk often comes reward. You have to be ready for both or… you’re not ready.
It’s ok to not be ready — if the sting of your previous rejection is still too fresh to risk such a feeling again. But don’t blame someone else for that fear. This new guy has nothing to do with that. And it’s unfair to project your fear onto him and to search for reasons not to trust him. If you aren’t ready, own that, and get off the dating track until you are. Because when you’re not ready and you’re projecting your fear onto others and looking for ways to judge their conduct or their intentions, you create baggage for them. YOU become the person who hurts and rejects. If this guy is as into you as he says he is and you aren’t able to invest in a relationship with him because you’re too afraid, that affects him. And you know how that might be manifesting? In anxiety. Like, anxiety in the bedroom. (Yes, it’s a real thing. Guys can have problems staying hard because they feel anxious and like they’re being judged. And there’s a real reason this guy could be feeling that. Anxiety caused by your reaction towards him makes a hell of a lot more sense than his not being attracted to you or being too hung up on an ex.)
A lot of this could be solved by communicating. And not over texts! Talk to him in person — reassure him how much you like him, tell him that your heart is still a little raw from the guy who rejected you before him, and express your concern that be may still have feelings for his ex. The two of you both need to feel safe with each other and assured that feelings are real and you both have similar intentions here. Until that happens, you will probably both continue to have anxiety, and you’ll likely both leave the relationship feeling stung and like the other never really liked you, which doesn’t sound like the case at all.
If you have a relationship/dating question I can help answer, you can send me your letters at wendy(AT)dearwendy.com.