Here are some things to watch out for:
1. Not being mature about sex.
The big question is when, and that’s a personal matter. If he doesn’t respect your wishes, he isn’t mature enough to be in a relationship, or isn’t really interested in one. In other words, if it seems like that’s all he’s interested in, that’s all he’s interested in. Make sure you’re reading on the same page about the intimacy if you get involved. You don’t want it to mean something to you, and mean nothing to him.
2. Ogling other women when with you.
There is simply no excuse for this. It is the poorest of dating etiquette. If he can’t control himself to avoid this (I don’t care if “that’s the way men are”), he doesn’t have what it takes to have a relationship.
3. He doesn’t seal the deal.
If he is taken with you on the first date, he should ask you for another date, preferably then, or the next day. He should certainly give you evidence that he enjoyed it - a txt msg or phone message the next day. If he waits too much longer, he isn’t that interested and he’s just calling you because he’s found time on his hands, and doesn’t know what else to do with himself, or he’s ambivalent. What we’re looking for here is honest enthusiasm.
4. Don’t do that yourself.
Let him do the pursuing. If you enjoyed his company you will have indicated this on the date - it’s hard to hide when you’re really have a good time. But don’t you be the one to txt msg the next day or call. And if he calls or emails, wait a while before you answer. (A man ready for a realtionship, loves the thrill of the hunt. Don’t deprive him of this.)
5. Excessive flattery regarding your looks.
It’s nice to hear you’re beautiful or gorgeous or sexy. Once. Maybe twice. More than that and he’s either that shallow, or he’s saying what has worked for him in the past to seduce women. He should move rapidly to talking about inner qualities, interesting movies, the scenery, or something of mutual interest. Complimenting you on other qualities is nice, too - like how organized you are, or how well you’ve thought something through. You aren’t just your body and you need to be getting evidence that he knows this. Otherwise, send your boobs to dinner and you stay home.
6. He’s not a good conversationalist.
Marriage, I always say, turns out to be an 8-hour car ride with no radio. Hardly likely these days, but you get my point. This includes showing a sense of humor. Conversations need to be guided, and he should be able to do this as well as you can. They should also be give-and-take, with true interest in what the other person is saying. He should not talk AT you or deliver a lecture. This shows ego-centrism, lack of social skills, or both. It won’t get any better. Marriage is also that car ride and you get a flat. Watch carefully how he handles little problems (wrong menu item, getting lost) during your date.
7. He talks about his ex, his broken heart and other traumas.
Stringers are usually ambivalent. They’ve been hurt and the wounds are still running sores. They don’t want a relationship, they just want a woman (any woman) to ease the pain. They don’t really know what they’re doing except for wanting sympathy. If you feel a pull to be his therapist or his mother, or to “fix” him, resist it. If he can’t talk about anything else but his sad past and heartbreak, do NOT mistake this for “vulnerability.” What he is doing is talking about himself. He is not available and he is also extremely selfish.
8. He has only one functioning “brain.”
And you know which one I’m talking about! Look for a man who is interested in relating to you both mentally and emotionally, not just physically.
9. He is too agreeable.
On the other hand, if he agrees with everything you say, he’s trying to get you into bed. Easy is sleazy. Look for a man self-confident enough to have opinions (that he knows are opinion, not gospel truth). This applies too, to setting up the next date. If he can’t orchestrate this, making the plans and showing initiative, there’s something wrong. This is the tricky part if you’ve been married before, because it is true - once you’re married, the woman does all this. But if he’s just out of a marriage and still in that mindset, he isn’t ready to date. He has to show you he’s standing squarely on his own two feet, and willing and able to do the work of dating (i.e., a relationship).
source: reviewchicago.com/2009/03/10/assessing-the-guys-long-term-dating-potential/