Is He Too Nice & That’s Why He Can’t Get a 2nd Date?

April 30, 2026 by No Comments

Name: Denny Laine
State: New York City
Age: 42
Comment: I think I’m too nice. I’m 42, single, never married. I’m on match.com, OKCupid, eHarmony and attend many Moxie/ATWYS singles parties. Lately I’ve been going on a lot of first dates. Usually these first dates would go really well.  By that I mean, it’s all about the amount of time they’re willing to spend with me.  These dates would start with a drink, then a full course meal, then about a 20 minute walk before we split up. At the end of the evening we’ve spent more than 3 hours with each other.  I figured if they’re not interested in me they would just leave and not drag it out (one date left after drinking half a cocktail – which is OK with me, we don’t end up wasting each other’s time and money). But the conversations always go well and I always find ourselves laughing. I check their non-verbal behavior as well. I hardly ever see their arms crossing. In fact we make plenty of eye contact and we hardly ever have any awkward pauses. Each date ends up with a hug and kiss on the cheek (more likely the kiss of death from my experience). Then afterwards I either not hear from them or they tell me they’re not interested.

I think it’s because I’m too nice! I don’t have an “edge.” I’m not a “bad boy.”

I don’t think it’s physical. The photos I have up on my sites are accurate. They are not misleading in anyway. Again if they feel they have been misled by an inaccurate photo I would assume they would just leave right away, which is OK by me.

I don’t have any major red flags: I’m fully employed, I own my own place, I’m well traveled, well read, I have alot of friends, good credit, not a virgin, STD and drug free, no prison records or anything, my parents have been together for 43 + years, I’m ready for a long term relationship. I don’t know. What else am I missing?

So I’ve come to the conclusion that maybe I’m too nice. It’s true that girls want bad boys (even from 30-42?). I may make a great dinner date but not a boyfriend.

One day I was talking to some friends about what we would do if we were set up on a blind date and we’re not too thrilled about seeing them in person. One female friend said to me “You’re a nice guy, you probably wouldn’t say anything to her.”  Then my last first date (a 35 year old midwife), upon leaving I said I had a great time and I would like to see her again. Then she mumbled “Yeah, my last two boyfriends weren’t nice and they didn’t work out.” When I asked her what she said she said “Oh nothing.”  Of course I never heard from her after that.

The same with speed dating. I get along great with everyone I’m sitting with but in the end none are interested.

So am I too nice? Is there such a thing? I can’t help it! I’m not going to change, I have three younger sisters and I’ve been raised to respect women. Any thoughts?

You’re asking a question that’s specifically designed for me and others to say that the problem isn’t you. So I’m not sure how genuine you are about wanting to know the answer to this dilemma. Everything about the way this letter is written says that you want to blame the women for being too this or that. And to some tiny degree you are right. I think part of the problem is that you’re available and I personally think many of the single women out there who say they want relationships actually don’t.  But with all the activities and methods that you’re using, you have to be meeting some women who are open and available. A lot, actually. Plus, the women who say that they don’t want a guy who is “too nice” are women who thrive off of chasing men that never want to be caught.You don’t want those women any way.

So what’s the deal there?

Well, I don’t think that it’s that you’re too nice. I think it’s that there is something about your demeanor that runs women off. And it has nothing to do with being too nice.

I think you’re being perceived as weak, as in trying too hard. I offer this as a suggestion because, if we’re going to be frank, you’re a bit of a whiner/sad sack. If any of what comes through in your letters is what women pick up on on your dates, then that’s your problem. There’s just no confidence in this letter. It’s very “Woe is me.” You seem to like to focus and dwell on the bad stuff. Are you this negative on dates? You might not even notice it or be aware of it. But there’s is something distinctly unattractive about a guy who seems sullen or disgruntled or anxious.

Something about your presentation does not convey strength and security. People like to say that women put emphasis on a man’s financial stability because it provides  a sense of security. To some degree, they’re right. But it’s not just financial security that we seek. (Especially now.) We want  a guy who is together and happy. We want  a man who isn’t delicate or fragile.

We also want a guy who doesn’t appear as though he’s going through the motions and has a been there, done that attitude. That’s what constant dating does to someone. We can tell when we’re on a date with that person. They just seem burnt out.

You are so far in your head that there is no way that you are present, really present, on any of these dates. You’re not enjoying yourself. You’re so focused on how she reacts and responds that you seem to be trying too hard and insecure.

I’ll also throw out there that you’re perceiving yourself as damaged somehow, and unconsciously going after women who seem damaged too. Like your mid-wife friend. That’s a recipe for disaster. Intentionally dating down like that doesn’t increasing your chances of finding someone who will stick around. Quite the opposite, because they’ve obviously been passed over for a reason.

Besides working on your attitude, you have to put yourself in a different environment. Try something else that doesn’t involve gathering a bunch of singles. Try an activity of some kind, or a special interest group. Start approaching women your age or a little older. It’s good to want to compete, and it’s a necessary evil. But you have to figure out what activities and locations provide less competition. Avoid the meat markety bar parties. Go for things that are more upscale. Branch out to groups that aren’t dating related, if only because the vibe will be different. Stop going out with the guy friends that usurp all the attention. In fact, stop hanging with your boys when you’re trying to meet women. Go off on your own.

Most importantly, stop feeling sorry for yourself and being so focused on what is “wrong” with you. While I’m sure there are things you need to tweak, not all the of the situations are about you. You can’t take everything so personally. There is enough evidence to suggest that some of the problem lies with you. Just not all of it.

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