Although the fear of rejection often stops a person from asking for a date, according to an eHarmony.com article, most singles would gladly accept a date invitation and would never think less of you for asking. Singles are often ready to say, "Yes" when asked on a date in an appropriate way and under the right circumstances. Timing is often key when it comes to someone accepting a date invitation.
Needing a Stand-In
As a single mom, there might be occasions when you don’t want to attend an event alone, such as a family outing where family members will ask why you aren’t dating. If you don’t have a steady dating partner, asking an acquaintance to attend an event with you is an option. When you ask your acquaintance to attend, be specific about why you need a date and what he will get out of it, such as a lovely meal or a night of terrific music. Don’t determine your self-worth based on the answer. The person you ask might not be free at the time of the event or dislike your suggestion. Accept his reply as only the answer to your date question. If you are interested in dating this person other than just for the specific event, be ready to suggest a different date idea.
If you don’t know whether someone likes you or not, suggesting an informal event that you can attend together can allow you to explore whether dating this person is an option. You might suggest the date in a way that makes your acquaintance think that he is asking you out, suggests Jeremy Nicholson, M.S.W., Ph.D. in a Psychology Today article. For example, ask your acquaintance if he’s seen the new blockbuster movie yet. He could respond by asking if you would like to go with him to check it out.
Another way to ask your friend out on a date without seeming to make it a date is to challenge him to come up with the best first date ever, suggests Nicholson. You might suggest that you think an awesome first date for single parents would be attending a fair with the kids -- and then challenge him to top your date. When he comes up with a suggestion that sounds like fun, ask if he would like to try out his suggestion to see how it works.
Rumor Has It
Rumors have a funny way of developing a life of their own, so if you can’t think of a way to ask your friend directly, suggest that you heard a rumor that he wanted to ask you out, suggests a Match.com article. If he hasn’t considered the idea, it proposes it to him in a way that doesn’t pressure either of you. He might think a date sounds like a good idea and propose something fun.